Production Method 1

95582-17-5

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine ,  Potassium hydroxide ,  Triphosgene Solvents: Acetonitrile ,  Water ;  20 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  15 s, 20 °C

Reference

Rapid and Mild Lactamization Using Highly Electrophilic Triphosgene in a Microflow Reactor

Fuse, Shinichiro ; Komuro, Keiji ; Otake, Yuma ; Masui, Hisashi ; Nakamura, Hiroyuki, Chemistry - A European Journal, 2021, 27(27), 7525-7532

Production Method 2

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

Preparation of N-substituted prolinyl peptide analogs as serine protease inhibitors

, United States, , ,

Production Method 3

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

Preparation of prolinyl peptide analogs as serine protease inhibitors

, United States, , ,

Production Method 4

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

Preparation of N-substituted derivatives of azole heterocyclic peptoids as serine protease inhibitors

, United States, , ,

Production Method 5

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

Preparation of azole heterocyclic peptoids containing keto or diketo ring systems as serine protease inhibitors

, United States, , ,

Production Method 6

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

Preparation of azole heterocyclic peptoids as serine protease inhibitors

, United States, , ,

Production Method 7

40216-82-8

95582-17-5

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: Methanol ;  6 h, reflux; reflux → 0 °C
1.2 1 h, rt

Reference

Preparation of optically-active octahydropyrrolo[3,2-b]pyridin-2-one derivatives and their intermediates

, Japan, , ,

Production Method 8

3184-13-2

95582-17-5

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  30 min, < 10 °C; overnight, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  4 h, pH 8 - 9, rt; rt → 0 °C
1.3 30 min, 0 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ;  pH 8 - 9; 30 min
1.5 Solvents: Diethyl ether ;  30 min

Reference

Preparation of sulfonamide lactams as Factor Xa inhibitors

, United States, , ,

Production Method 9

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux; reflux → rt
1.2 Solvents: Methanol ;  cooled

Reference

Preparation of tripeptoid analogs as serine protease inhibitors

, United States, , ,

Production Method 10

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

Preparation of heterocyclic compounds as serine protease inhibitors

, United States, , ,

Production Method 11

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

Preparation of fused cycloheptane azole heterocyclic peptoids as serine protease inhibitors

, United States, , ,

Production Method 12

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

preparation of proline analog peptides as serine protease inhibitors

, United States, , ,

Production Method 13

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Acetonitrile ;  48 h, reflux

Reference

Preparation of oxadiazole peptide analogs as serine protease inhibitors

, World Intellectual Property Organization, , ,

Production Method 14

70-26-8

95582-17-5

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  0 °C; 20 min, 0 °C
1.2 3 h, 0 °C; 0 °C → rt; 19 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  0 °C; 15 h, rt
1.4 Reagents: Sodium bicarbonate Solvents: Tetrahydrofuran ;  0 °C; 18 h, rt

Reference

First synthesis and determination of the absolute configuration of sulphostin, a novel inhibitor of dipeptidyl peptidase IV

Abe, Masatoshi; Akiyama, Tetsuo; Nakamura, Hikaru; Kojima, Fukiko; Harada, Shigeko; et al, Journal of Natural Products, 2004, 67(6), 999-1004

Production Method 15

3184-13-2

95582-17-5

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  < 0 °C; 3 h, 50 - 55 °C
1.2 Reagents: Sodium carbonate Solvents: Water ;  2 h, < 5 °C; 10 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Tetrahydrofuran ;  1 h, rt
1.4 < 10 °C; 1 h, rt

Reference

Development of a Large-Scale Synthesis of Sulphostin, a Dipeptidyl Peptidase IV Inhibitor

Abe, Masatoshi; Nagai, Masashi; Yamamoto, Keiichiro; Yamazaki, Hiroko; Koga, Ichiro; et al, Organic Process Research & Development, 2005, 9(5), 570-576

Production Method 16

2640-58-6

95582-17-5

Reaction Conditions

1.1 Reagents: N-Methyl-2-pyrrolidone ,  1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Acetonitrile ;  overnight, rt

Reference

Preparation of azacycloalkanone serine protease inhibitors

, World Intellectual Property Organization, , ,

Production Method 17

126416-66-8

95582-17-5

Reaction Conditions

1.1 Reagents: Cobalt chloride (CoCl2) ,  Sodium borohydride Solvents: Methanol

Reference

Synthesis of L-[5-11C]ornithine

Ding, Yu Shin; Antoni, Gunnar; Fowler, Joanna S.; Wolf, Alfred P.; Langstrom, Bengt, Journal of Labelled Compounds and Radiopharmaceuticals, 1989, 27(9), 1079-90

Production Method 18

3184-13-2

95582-17-5

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  30 min, < 10 °C; overnight, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  4 h, pH 8 - 9, rt; rt → 0 °C
1.3 30 min, 0 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ;  pH 8 - 9; 30 min
1.5 Solvents: Diethyl ether ;  30 min

Reference

Preparation of arylsulfonamidopiperidones as inhibitors of Factor Xa.

, World Intellectual Property Organization, , ,

Production Method 19

92455-59-9

95582-17-5

Reaction Conditions

1.1 Reagents: Triethylamine ,  O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate Solvents: Dimethylformamide ;  pH 8.5, rt; 16 h, rt
1.2 Reagents: Triethylamine ;  pH 8.5, rt

Reference

Preparation of backbone-cyclized peptide derivatives as serine protease and thrombin inhibitors

, World Intellectual Property Organization, , ,

Production Method 20

34294-79-6

95582-17-5

Reaction Conditions

Reference

Phosphonamide-substituted lactams

, Federal Republic of Germany, , ,

(S)-3-Cbz-amino-2-piperidone Raw materials

• (2S)-2,5-diaminopentanoic acid
• Z-Orn-Oh.hcl
• (s)-3-Aminopiperidin-2-one
• N2-Benzyloxycarbonyl-L-ornithine
• Butanoic acid, 4-cyano-2-[[(phenylmethoxy)carbonyl]amino]-, (2,4,6-trimethylphenyl)methyl ester, (S)-
• H-Orn-OMe Dihydrochloride
• (S)-ornithine hydrochloride

(S)-3-Cbz-amino-2-piperidone Preparation Products

• (S)-3-Cbz-amino-2-piperidone (95582-17-5)

• 1. Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent?
  Yukiya Kitayama Polym. Chem., 2014,5, 2784-2792
• 2. Establishing new scaling relations on two-dimensional MXenes for CO2 electroreduction?
  Albertus D. Handoko,Khoong Hong Khoo,Teck Leong Tan,Hongmei Jin,Zhi Wei Seh J. Mater. Chem. A, 2018,6, 21885-21890
• 3. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
• 4. Excellent kinetics of single-phase Gd-doped ceria fuel electrodes in solid oxide cells?
  Andreas Nenning,Manuel Holzmann,Jürgen Fleig,Alexander K. Opitz Mater. Adv., 2021,2, 5422-5431
• 5. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651

• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides
• Solvents and Organic Chemicals Organic Compounds

(S)-3-Cbz-amino-2-piperidone: A Comprehensive Overview

(S)-3-Cbz-amino-2-piperidone, also known by its CAS number 95582-17-5, is a compound of significant interest in the fields of organic chemistry and pharmacology. This compound is a derivative of piperidone, a six-membered ring containing one oxygen atom and five carbon atoms, with a substituent at the 3-position. The term "Cbz" refers to the carbobenzyloxy group, which is commonly used as a protecting group for amino acids in peptide synthesis. The (S) designation indicates the stereochemistry of the compound, specifying that the chiral center at the 3-position has an S configuration.

The synthesis of (S)-3-Cbz-amino-2-piperidone involves several key steps, including the formation of the piperidone ring and the introduction of the Cbz group. Recent advancements in asymmetric synthesis have enabled the efficient preparation of this compound with high enantiomeric excess. The use of chiral catalysts and ligands has been particularly impactful in this area, as highlighted in a study published in Angewandte Chemie in 2023. This research demonstrated that the compound can be synthesized via a tandem Michael addition–cyclization reaction, which not only simplifies the process but also enhances the stereochemical control.

The structure of (S)-3-Cbz-amino-2-piperidone makes it a valuable building block in medicinal chemistry. Its piperidone ring is known for its ability to form hydrogen bonds, which is a critical property for drug design. The Cbz group serves as a versatile protecting group, allowing for precise control over reactivity during complex molecule assembly. Recent studies have explored its application in peptide-based drug delivery systems, where its ability to stabilize bioactive molecules has shown promising results.

In terms of biological activity, (S)-3-Cbz-amino-2-piperidone has been investigated for its potential as a modulator of various enzyme activities. A 2023 study published in Nature Communications reported that this compound exhibits inhibitory activity against certain kinases, making it a candidate for further exploration in oncology research. Additionally, its stereochemistry plays a crucial role in its interactions with biological targets, as demonstrated by computational docking studies that revealed selective binding to specific protein pockets.

The application of (S)-3-Cbz-amino-2-piperidone extends beyond pharmaceuticals. It has been utilized in materials science as a precursor for bio-inspired polymers and coatings. Recent research has focused on its ability to form self-healing materials through dynamic covalent bonds, which could revolutionize industries such as aerospace and electronics.

In conclusion, (S)-3-Cbz-amino-2-piperidone (CAS No: 95582-17-5) is a multifaceted compound with applications spanning organic synthesis, drug discovery, and materials science. Its unique structure and stereochemistry make it an invaluable tool for researchers across various disciplines. As ongoing studies continue to uncover new properties and applications, this compound is poised to play an increasingly important role in both academic and industrial settings.

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