Cas no 83509-88-0 ((S)-3-(Cbz-amino)butanoic Acid)

(S)-3-(Cbz-amino)butanoic Acid structure

83509-88-0 structure

Product Name:(S)-3-(Cbz-amino)butanoic Acid

CAS No:83509-88-0

MF:C₁₂H₁₅NO₄

MW:237.251803636551

MDL:MFCD08277048

CID:708890

PubChem ID:11042754

Update Time:2024-10-26

(S)-3-(Cbz-amino)butanoic Acid Chemical and Physical Properties

Names and Identifiers

- (S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid
- (3S)-3-(phenylmethoxycarbonylamino)butanoic acid
- Butanoic acid,3-[[(phenylmethoxy)carbonyl]amino]-, (3S)-
- Z-Β-HOMOALA-OH
- (3S)-3-[[(Phenylmethoxy)carbonyl]amino]butanoic acid (ACI)
- Butanoic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, (S)- (ZCI)
- (S)-3-(((Benzyloxy)carbonyl)amino)butanoicacid
- (s)-3-(Cbz-amino)butanoic acid
- (S)-3-(Cbz-amino)butyric Acid
- (S)-3-Benzyloxycarbonylaminobutyric acid
- CS-0095471
- AKOS016844014
- Z-beta-Homoala-OH, >=98.0% (HPLC)
- MFCD08277048
- AS-37874
- DS-019249
- (3S)-3-{[(Benzyloxy)carbonyl]amino}butanoic acid
- Z--HOMOALA-OH
- A-Homoala-OH
- DTXSID50453082
- Z-beta-Homoala-OH
- 83509-88-0
- EN300-816816
- Z-
- SCHEMBL5194569
- (S)-3-(Cbz-amino)butanoic Acid
- MDL： MFCD08277048
- Inchi： 1S/C12H15NO4/c1-9(7-11(14)15)13-12(16)17-8-10-5-3-2-4-6-10/h2-6,9H,7-8H2,1H3,(H,13,16)(H,14,15)/t9-/m0/s1
- InChI Key： HYWJKPFAIAWVHP-VIFPVBQESA-N
- SMILES： C(C1C=CC=CC=1)OC(=O)N[C@@H](C)CC(=O)O

Computed Properties

Exact Mass: 237.10010796g/mol
Monoisotopic Mass: 237.10010796g/mol
Isotope Atom Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 5
Heavy Atom Count: 17
Rotatable Bond Count: 7
Complexity: 261
Covalently-Bonded Unit Count: 1
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count : 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
XLogP3: 1.4
Topological Polar Surface Area: 75.6?2

Experimental Properties

Boiling Point: 435.6±38.0℃ at 760 mmHg

(S)-3-(Cbz-amino)butanoic Acid Security Information

Hazardous Material transportation number：NONH for all modes of transport
WGK Germany：3
FLUKA BRAND F CODES：10

(S)-3-(Cbz-amino)butanoic Acid Pricemore >>

Related Categories	No.	Product Name	Cas No.	Purity	Specification	Price	update time
Chemenu	CM185649-5g	(S)-3-(((benzyloxy)carbonyl)amino)butanoic acid	83509-88-0	95+%	5g	$911	2021-06-09
TRC	C228118-10mg	(S)-3-(Cbz-amino)butanoic Acid	83509-88-0		10mg	$ 50.00	2022-04-01
TRC	C228118-50mg	(S)-3-(Cbz-amino)butanoic Acid	83509-88-0		50mg	$ 115.00	2022-04-01
TRC	C228118-100mg	(S)-3-(Cbz-amino)butanoic Acid	83509-88-0		100mg	$ 185.00	2022-04-01
SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd.	S906754-5g	(S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid	83509-88-0	95%	5g	4,743.00	2021-05-17
Chemenu	CM185649-5g	(S)-3-(((benzyloxy)carbonyl)amino)butanoic acid	83509-88-0	95+%	5g	$450	2023-02-18
Ambeed	A238127-250mg	(S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid	83509-88-0	97%	250mg	$15.0	2025-04-16
Ambeed	A238127-1g	(S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid	83509-88-0	97%	1g	$43.0	2025-04-16
Ambeed	A238127-5g	(S)-3-(((Benzyloxy)carbonyl)amino)butanoic acid	83509-88-0	97%	5g	$206.0	2025-04-16
SHANG HAI XIAN DING Biotechnology Co., Ltd.	B-LC941-200mg	(S)-3-(Cbz-amino)butanoic Acid	83509-88-0	97%	200mg	542.0CNY	2021-07-17

(S)-3-(Cbz-amino)butanoic Acid Production Method

Production Method 1

158851-30-0

83509-88-0

Reaction Conditions

1.1 Solvents: Dichloromethane ; rt → 0 °C
1.2 Reagents: Trifluoroacetic acid ; 0 °C; 2 h, rt
1.3 Reagents: Sodium hydroxide Solvents: Water ; 1 h, 5 °C; 1 h, 5 °C

Reference

Syntheses and CD-spectroscopic investigations of longer-chain β-peptides: Preparation by solid-phase couplings of single amino acids, dipeptides, and tripeptides

Arvidsson, Per I.; et al, Helvetica Chimica Acta, 2003, 86(5), 1522-1553

Production Method 2

172695-22-6

83509-88-0

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ; 12 h, reflux; cooled
1.2 Reagents: Sodium hydroxide Solvents: Water ; pH 7
1.3 Reagents: Sodium hydroxide Solvents: Water ; rt → 0 °C
1.4 0.5 h, 0 °C; 0 °C → rt; 2 h, rt

Reference

Chemoenzymic synthesis of 4-amino-2-hydroxy acids: A comparison of mutant and wild-type oxidoreductases

Sutherland, Andrew; et al, Journal of Organic Chemistry, 1998, 63(22), 7764-7769

Production Method 3

1142-20-7

80-11-5

83509-88-0

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Methanol , Water ; rt
1.2 Reagents: Acetic acid ; rt
1.3 Reagents: Tributylamine , Ethyl chloroformate Solvents: Tetrahydrofuran ; 6.7 min, rt
1.4 80 min, rt
1.5 Reagents: Water Solvents: Tetrahydrofuran ; 10 min, rt

Reference

Continuous flow synthesis of β-amino acids from α-amino acids via Arndt-Eistert homologation

Pinho, Vagner D.; et al, RSC Advances, 2014, 4(70), 37419-37422

Production Method 4

79069-13-9

83509-88-0

Reaction Conditions

1.1 Reagents: Tosyl chloride , Triethylamine , 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 0 °C; 0 °C → rt; overnight, rt
1.2 Solvents: Dimethylformamide ; 24 h, rt
2.1 Reagents: Hydrochloric acid Solvents: Water ; 12 h, reflux; cooled
2.2 Reagents: Sodium hydroxide Solvents: Water ; pH 7
2.3 Reagents: Sodium hydroxide Solvents: Water ; rt → 0 °C
2.4 0.5 h, 0 °C; 0 °C → rt; 2 h, rt

Reference

Chemoenzymic synthesis of 4-amino-2-hydroxy acids: A comparison of mutant and wild-type oxidoreductases

Sutherland, Andrew; et al, Journal of Organic Chemistry, 1998, 63(22), 7764-7769

Production Method 5

83509-88-0

Reaction Conditions

1.1 Reagents: Acetic anhydride Catalysts: 4-(Dimethylamino)pyridine Solvents: Diethyl ether ; 2 h, 25 °C
1.2 Reagents: Sodium borohydride Solvents: Ethanol ; 2 h, 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; acidified
2.1 Reagents: Acetic acid , Sodium nitrite Solvents: Dimethyl sulfoxide ; 20 h, 25 °C → 40 °C; 40 °C → 25 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ; 15 min, 25 °C

Reference

A mild multistep conversion of N-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction

Sleebs, Brad E.; et al, Synlett, 2013, 24(6), 747-751

Production Method 6

26607-51-2

83509-88-0

Reaction Conditions

1.1 Reagents: Diisopropylethylamine , O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate Solvents: Dimethylformamide , Tetrahydrofuran ; 0 °C
2.1 Reagents: Silver benzoate Solvents: 1,4-Dioxane , Water ; 5 h, 70 °C

Reference

Synthesis of β-Amino Acids: 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium Tetrafluoroborate (TBTU) for Activation of Fmoc-/Boc-/Z-α-Amino Acids

Patil, Basanagoud S.; et al, Synthetic Communications, 2003, 33(18), 3089-3096

Production Method 7

67919-80-6

83509-88-0

Reaction Conditions

1.1 Solvents: Tetrahydrofuran , Water ; rt → -25 °C; 15 min, -25 °C
1.2 Reagents: Triethylamine Catalysts: Silver trifluoroacetate ; 5 h, -25 °C → rt
2.1 Solvents: Dichloromethane ; rt → 0 °C
2.2 Reagents: Trifluoroacetic acid ; 0 °C; 2 h, rt
2.3 Reagents: Sodium hydroxide Solvents: Water ; 1 h, 5 °C; 1 h, 5 °C

Reference

Syntheses and CD-spectroscopic investigations of longer-chain β-peptides: Preparation by solid-phase couplings of single amino acids, dipeptides, and tripeptides

Arvidsson, Per I.; et al, Helvetica Chimica Acta, 2003, 86(5), 1522-1553

Production Method 8

16750-40-6

83509-88-0

Reaction Conditions

1.1 Solvents: Water ; 0.5 h, pH 7, 30 °C
1.2 100 min, 30 °C
1.3 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran , Water ; overnight, 0 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ; pH 12
1.5 Reagents: Hydrochloric acid Solvents: Water ; pH 4

Reference

Nitrile Biotransformations for the Synthesis of Highly Enantioenriched β-Hydroxy and β-Amino Acid and Amide Derivatives: A General and Simple but Powerful and Efficient Benzyl Protection Strategy To Increase Enantioselectivity of the Amidase

Ma, Da-You; et al, Journal of Organic Chemistry, 2008, 73(11), 4087-4091

Production Method 9

67865-68-3

83509-88-0

Reaction Conditions

1.1 Reagents: Silica Catalysts: Silver triflate Solvents: Ethyl acetate ; 15 min, 50 °C

Reference

Exceptionally simple homologation of protected α- to β-amino acids in the presence of silica gel

Koch, Karen; et al, Synthetic Communications, 2005, 35(21), 2789-2794

Production Method 10

67865-68-3

83509-88-0

Reaction Conditions

1.1 Catalysts: Silver benzoate Solvents: 1,4-Dioxane , Water ; 6 h, reflux
1.2 Reagents: Sodium carbonate Solvents: Water ; 1 h, rt
1.3 Reagents: Citric acid , Hydrochloric acid Solvents: Water ; pH 2, rt

Reference

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Zheng, Yongpeng; et al, Tetrahedron, 2014, 70(34), 5197-5206

Production Method 11

67865-68-3

83509-88-0

Reaction Conditions

1.1 Reagents: Water Catalysts: Silver trifluoroacetate Solvents: 1,4-Dioxane ; 30 min, rt

Reference

Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones

Hughes, Andrew B.; et al, Helvetica Chimica Acta, 2006, 89(11), 2611-2637

Production Method 12

1445444-14-3

83509-88-0

Reaction Conditions

1.1 Reagents: Acetic acid , Sodium nitrite Solvents: Dimethyl sulfoxide ; 20 h, 25 °C → 40 °C; 40 °C → 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ; 15 min, 25 °C

Reference

A mild multistep conversion of N-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction

Sleebs, Brad E.; et al, Synlett, 2013, 24(6), 747-751

Production Method 13

3775-72-2

83509-88-0

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ; 30 min, 0 °C; 0 °C → rt; 2 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 2

Reference

Design and Synthesis of C5 Methylated L-Arginine Analogues as Active Site Probes for Nitric Oxide Synthase

Martin, Nathaniel I.; et al, Journal of the American Chemical Society, 2007, 129(41), 12563-12570

Production Method 14

1142-20-7

83509-88-0

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine , Ethyl chloroformate Solvents: Tetrahydrofuran ; rt → -15 °C; 15 min, -15 °C
1.2 Solvents: Dichloromethane ; -15 °C; -15 °C → rt
2.1 Reagents: Water Catalysts: Silver trifluoroacetate Solvents: 1,4-Dioxane ; 30 min, rt

Reference

Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones

Hughes, Andrew B.; et al, Helvetica Chimica Acta, 2006, 89(11), 2611-2637

Production Method 15

1142-20-7

83509-88-0

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine , Ethyl chloroformate Solvents: Tetrahydrofuran ; 15 min, 0 °C
1.2 Solvents: Diethyl ether ; 0 °C; 0 °C → rt; rt
1.3 Reagents: Acetic acid ; rt
2.1 Catalysts: Silver benzoate Solvents: 1,4-Dioxane , Water ; 6 h, reflux
2.2 Reagents: Sodium carbonate Solvents: Water ; 1 h, rt
2.3 Reagents: Citric acid , Hydrochloric acid Solvents: Water ; pH 2, rt

Reference

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Zheng, Yongpeng; et al, Tetrahedron, 2014, 70(34), 5197-5206

Production Method 16

111955-03-4

83509-88-0

Reaction Conditions

1.1 Reagents: Potassium fluoride Solvents: Isopropanol ; 0 °C; 0 °C → 25 °C; 8 h, 25 °C
2.1 Reagents: Acetic anhydride Catalysts: 4-(Dimethylamino)pyridine Solvents: Diethyl ether ; 2 h, 25 °C
2.2 Reagents: Sodium borohydride Solvents: Ethanol ; 2 h, 0 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ; acidified
3.1 Reagents: Acetic acid , Sodium nitrite Solvents: Dimethyl sulfoxide ; 20 h, 25 °C → 40 °C; 40 °C → 25 °C
3.2 Reagents: Hydrochloric acid Solvents: Water ; 15 min, 25 °C

Reference

A mild multistep conversion of N-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction

Sleebs, Brad E.; et al, Synlett, 2013, 24(6), 747-751

Production Method 17

15761-38-3

83509-88-0

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ; rt → -25 °C
1.2 Reagents: Triethylamine , Isobutyl chloroformate ; 30 min, -25 °C
1.3 Solvents: Diethyl ether ; 16 h, -25 °C
1.4 Reagents: Acetic acid
2.1 Solvents: Tetrahydrofuran , Water ; rt → -25 °C; 15 min, -25 °C
2.2 Reagents: Triethylamine Catalysts: Silver trifluoroacetate ; 5 h, -25 °C → rt
3.1 Solvents: Dichloromethane ; rt → 0 °C
3.2 Reagents: Trifluoroacetic acid ; 0 °C; 2 h, rt
3.3 Reagents: Sodium hydroxide Solvents: Water ; 1 h, 5 °C; 1 h, 5 °C

Reference

Syntheses and CD-spectroscopic investigations of longer-chain β-peptides: Preparation by solid-phase couplings of single amino acids, dipeptides, and tripeptides

Arvidsson, Per I.; et al, Helvetica Chimica Acta, 2003, 86(5), 1522-1553

Production Method 18

15761-38-3

83509-88-0

Reaction Conditions

1.1 Reagents: Triethylamine , Ethyl chloroformate Solvents: Tetrahydrofuran ; 0.25 h, 0 °C
1.2 Reagents: Sodium borohydride Solvents: Water ; 0.5 h, 0 °C; 0 °C → rt; 2 h, rt
2.1 Reagents: Tosyl chloride , Triethylamine , 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 0 °C; 0 °C → rt; overnight, rt
2.2 Solvents: Dimethylformamide ; 24 h, rt
3.1 Reagents: Hydrochloric acid Solvents: Water ; 12 h, reflux; cooled
3.2 Reagents: Sodium hydroxide Solvents: Water ; pH 7
3.3 Reagents: Sodium hydroxide Solvents: Water ; rt → 0 °C
3.4 0.5 h, 0 °C; 0 °C → rt; 2 h, rt

Reference

Chemoenzymic synthesis of 4-amino-2-hydroxy acids: A comparison of mutant and wild-type oxidoreductases

Sutherland, Andrew; et al, Journal of Organic Chemistry, 1998, 63(22), 7764-7769

Production Method 19

24424-99-5

56-41-7

83509-88-0

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ; rt → 0 °C; 0.5 h, 0 °C; 0 °C → rt; 2 h, rt
2.1 Reagents: Triethylamine , Ethyl chloroformate Solvents: Tetrahydrofuran ; 0.25 h, 0 °C
2.2 Reagents: Sodium borohydride Solvents: Water ; 0.5 h, 0 °C; 0 °C → rt; 2 h, rt
3.1 Reagents: Tosyl chloride , Triethylamine , 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 0 °C; 0 °C → rt; overnight, rt
3.2 Solvents: Dimethylformamide ; 24 h, rt
4.1 Reagents: Hydrochloric acid Solvents: Water ; 12 h, reflux; cooled
4.2 Reagents: Sodium hydroxide Solvents: Water ; pH 7
4.3 Reagents: Sodium hydroxide Solvents: Water ; rt → 0 °C
4.4 0.5 h, 0 °C; 0 °C → rt; 2 h, rt

Reference

Chemoenzymic synthesis of 4-amino-2-hydroxy acids: A comparison of mutant and wild-type oxidoreductases

Sutherland, Andrew; et al, Journal of Organic Chemistry, 1998, 63(22), 7764-7769

Production Method 20

66674-16-6

83509-88-0

Reaction Conditions

1.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 15 min, -78 °C
1.2 Solvents: Dichloromethane ; 10 min, -78 °C; 10 min, -78 °C
1.3 Reagents: Triethylamine Solvents: Dichloromethane ; 15 min, -78 °C; 20 min, -78 °C
2.1 Reagents: Potassium fluoride Solvents: Isopropanol ; 0 °C; 0 °C → 25 °C; 8 h, 25 °C
3.1 Reagents: Acetic anhydride Catalysts: 4-(Dimethylamino)pyridine Solvents: Diethyl ether ; 2 h, 25 °C
3.2 Reagents: Sodium borohydride Solvents: Ethanol ; 2 h, 0 °C
3.3 Reagents: Hydrochloric acid Solvents: Water ; acidified
4.1 Reagents: Acetic acid , Sodium nitrite Solvents: Dimethyl sulfoxide ; 20 h, 25 °C → 40 °C; 40 °C → 25 °C
4.2 Reagents: Hydrochloric acid Solvents: Water ; 15 min, 25 °C

Reference

A mild multistep conversion of N-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction

Sleebs, Brad E.; et al, Synlett, 2013, 24(6), 747-751

Production Method 21

1142-20-7

83509-88-0

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine , Ethyl chloroformate Solvents: Tetrahydrofuran ; 15 min, -15 °C
1.2 Reagents: Sodium borohydride Solvents: Water ; 15 min, -15 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; neutralized
2.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 15 min, -78 °C
2.2 Solvents: Dichloromethane ; 10 min, -78 °C; 10 min, -78 °C
2.3 Reagents: Triethylamine Solvents: Dichloromethane ; 15 min, -78 °C; 20 min, -78 °C
3.1 Reagents: Potassium fluoride Solvents: Isopropanol ; 0 °C; 0 °C → 25 °C; 8 h, 25 °C
4.1 Reagents: Acetic anhydride Catalysts: 4-(Dimethylamino)pyridine Solvents: Diethyl ether ; 2 h, 25 °C
4.2 Reagents: Sodium borohydride Solvents: Ethanol ; 2 h, 0 °C
4.3 Reagents: Hydrochloric acid Solvents: Water ; acidified
5.1 Reagents: Acetic acid , Sodium nitrite Solvents: Dimethyl sulfoxide ; 20 h, 25 °C → 40 °C; 40 °C → 25 °C
5.2 Reagents: Hydrochloric acid Solvents: Water ; 15 min, 25 °C

Reference

A mild multistep conversion of N-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction

Sleebs, Brad E.; et al, Synlett, 2013, 24(6), 747-751

(S)-3-(Cbz-amino)butanoic Acid Raw materials

(S)-3-(Cbz-amino)butanoic Acid Preparation Products

(S)-3-(Cbz-amino)butanoic Acid (83509-88-0)

(S)-3-(Cbz-amino)butanoic Acid Related Literature

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83509-88-0 ((S)-3-(Cbz-amino)butanoic Acid) Related Products

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Cas no 83509-88-0 ((S)-3-(Cbz-amino)butanoic Acid)

(S)-3-(Cbz-amino)butanoic Acid Chemical and Physical Properties

Names and Identifiers

Computed Properties

Experimental Properties

(S)-3-(Cbz-amino)butanoic Acid Security Information

(S)-3-(Cbz-amino)butanoic Acid Pricemore >>

(S)-3-(Cbz-amino)butanoic Acid Production Method

Production Method 1

Production Method 2

Production Method 3

Production Method 4

Production Method 5

Production Method 6

Production Method 7

Production Method 8

Production Method 9

Production Method 10

Production Method 11

Production Method 12

Production Method 13

Production Method 14

Production Method 15

Production Method 16

Production Method 17

Production Method 18

Production Method 19

Production Method 20

Production Method 21

(S)-3-(Cbz-amino)butanoic Acid Raw materials

(S)-3-(Cbz-amino)butanoic Acid Preparation Products

(S)-3-(Cbz-amino)butanoic Acid Related Literature

83509-88-0 ((S)-3-(Cbz-amino)butanoic Acid) Related Products