Cas no 86299-47-0 ((2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid)

(2Z)-2-(2-Aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid is a specialized synthetic intermediate primarily used in the pharmaceutical and fine chemical industries. Its key structural features include a 2-aminothiazole moiety and a tert-butoxycarbonyl-protected imino-acetic acid group, making it valuable for the synthesis of β-lactam antibiotics and other bioactive compounds. The compound exhibits high purity and stability under controlled conditions, ensuring reliable performance in complex reactions. Its well-defined stereochemistry (Z-configuration) and functional group compatibility enhance its utility in precision organic synthesis. This intermediate is particularly advantageous for researchers requiring regioselective modifications in drug development, offering a versatile scaffold for further derivatization. Proper handling under inert conditions is recommended to preserve its reactivity.
(2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid structure
86299-47-0 structure
Product Name:(2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid
CAS No:86299-47-0
MF:C13H19N3O5S
MW:329.37206196785
MDL:MFCD00071569
CID:60966
PubChem ID:6242497
Update Time:2025-10-27

(2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid Chemical and Physical Properties

Names and Identifiers

    • (Z)-2-(2-Aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetic acid
    • 2-(2-AMINOTHIAZOLE-4-YL)-2-[Z-1-(T-BUTOXY CARBONYL)-1-METHYL ETHOXY]-IMINO ACETIC ACID
    • 2-Amino-alpha-[[2-(1,1-dimethyl-ethoxy)-1,1-dimethyl-2-oxo-ethoxy]imino]-4-thiazoleacetic acid ethyl ester
    • 2-AMINO-ALPHA-[[2-(1,1-DIMETHYL-ETHOXY)-1,1-DIMETHYL-2-OXO-ETHOXY]IMINO]-,ETHYL ESTER,4-THIAZOLEACETIC ACID
    • ATIBAA
    • ATTBA
    • ETHYL 2-(2-AMINOTHIAZOL-4-YL)-2-(1-TERT-BUTOXYCARBONYL-1-METHYL)-ETHOXYIMINOACETATE
    • ETHYL 2-(2-AMINOTHIAZOLE-4-YL)-2-(1-TERT-BUTOXYCARBONYL-1-METHYL)-ETHOXYIMINOACETATE
    • TBA
    • (Z)-2-(2-AMINOTHIAZOL-4-YL)-2-(1-T-BUTOXYCARBONYL-1-METHYL)ETHOXYIMINOACETIC ACID
    • (Z)-2-(2-TERT-BUTOXYCARBONYLPROP-2-OXYIMINO)-2-(2-AMINOTHIAZOLE-4-YL)ACETIC ACID
    • (Z)-2-AMINO-ALPHA-[1-(TERT-BUTOXYCARBONYL)]-1-1-METHYLETHOXYIMINO-4-THIAZOLACETIC ACID
    • (Z)-2-AMINO-ALPHA-[1-(TERT-BUTOXYCARBONYL)]-1-1-METHYLETHOXYIMINO-4-THIAZOLEACETIC ACID
    • (Z)-2-AMINO-ALPHA-[1-(TERT-BUTOXYCARBONYL)-1-METHYLETHOXYIMINO]-4-THIAZOLEACETIC ACID
    • (Z)-((2-AMINOTHIAZOLE-4-YL)-2-(TERT-BUTOXYCARBONYL)ISOPROPOXYIMINO)ACETIC ACID
    • (Z)-(2-Aminothiazol-4-yl)-2-(tert-butoxycarbonyl)isopropoxyiminoaceticacid
    • (Z)-2-(2-tert-Butoxycarbonylprop-2-Oxyimino)-2-(2-Amino-thiazol-4-yl) Acetic Acid
    • (Z)-2-(2-aminothiazol-4-yl)-2-(2-t-butoxycarbonylprop-2-oxyimino)-acetic acid
    • (Z)-2-(2-Aminothiazol-4-yl)-2-[(1-tert-butoxycarbonyl-1-methylethoxy)imino]acetic Acid
    • (2-Amino-1,3-thiazol-4-yl)[(2-tert-butoxy-2-oxoethoxy)imino]acetic acid
    • (Z)-(2-Aminothiazole-4-yl)-2-(tert-butoxycarbonyl)isopropoxyimino)aceticacid
    • (Z)-2-(2-Aminothiazol-4-yl)-2-(2-T-butoxycarbonylmethoxyimino) Acetic Acid
    • (Z)-2-Amino-alpha-[1-(tert-butoxycarbonyl)]-1-methylethoxyimino-4-thiazolacetic acid
    • (Z)-2-Amino-α-[1-(tert-butoxycarbonyl)]-1-methylethoxyimino-4-thiazolacetic acid
    • AT-TBA
    • 4-Thiazoleaceticacid, 2-amino-a-[[2-(1,1-dimethylethoxy)-1,1-dimethyl-2-oxoethoxy]imino]-,(Z)-
    • (Z)-(2-Aminothiazol-4-yl)-2-(2-tert-butoxycarbonyl-2-propoxyimino)aceticacid
    • (Z)-2-(2-Aminothiazol-4-yl)-2-[(1-tert-butoxycarbonyl-1-methylethoxy)imino]aceticacid
    • C13H19N3O5S
    • (2Z)-2-(2-amino(1,3-thiazol-4-yl))-3-{1
    • (2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid
    • (αZ)-2-Amino-α-[[2-(1,1-dimethylethoxy)-1,1-dimethyl-2-oxoethoxy]imino]-4-thiazoleacetic acid (ACI)
    • 4-Thiazoleacetic acid, 2-amino-α-[[2-(1,1-dimethylethoxy)-1,1-dimethyl-2-oxoethoxy]imino]-, (Z)- (ZCI)
    • (Z)-(2-Aminothiazol-4-yl)-2-(2-tert-butoxycarbonyl-2-propoxyimino)acetic acid
    • AS-13249
    • (Z)-2-(2-Aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)aceticacid
    • CS-W006175
    • (Z)-2-(2-tert-Butoxycarbonylprop-2-oxyimino)-2-(2-amino-thiazol-4-yl)acetic acid
    • (Z)-2-amino-alpha-[1-(tert-butoxycarbonyl)]-1-1-methylethoxyimino-4
    • (2-amino-1,3-thiazol-4-yl)[(2-tert-butoxy-1,1-dimethyl-2-oxoethoxy)imino]acetic acid
    • SCHEMBL2833601
    • CHEMBL3212852
    • LS-14237
    • (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetic acid
    • (Z)-(2-Amino-alpha-[1-(tert-butoxycarbonyl)]-1-methylethoxyimino-4-thiazolacetic acid
    • AG-664/13102029
    • SR-01000314746
    • AKOS000520616
    • SR-01000314746-1
    • MFCD00071569
    • SMR000274233
    • AC-075
    • 86299-47-0
    • MLS000714253
    • J-502583
    • MDL： MFCD00071569
    • Inchi： 1S/C13H19N3O5S/c1-12(2,3)20-10(19)13(4,5)21-16-8(9(17)18)7-6-22-11(14)15-7/h6H,1-5H3,(H2,14,15)(H,17,18)/b16-8-
    • InChI Key： FNRZBOJFRDVEOG-PXNMLYILSA-N
    • SMILES： C(/C1N=C(N)SC=1)(\C(=O)O)=N\OC(C)(C)C(=O)OC(C)(C)C

Computed Properties

  • Exact Mass: 329.10500
  • Monoisotopic Mass: 329.105
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 9
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 7
  • Complexity: 473
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 152
  • Surface Charge: -1
  • Tautomer Count: 2
  • XLogP3: 3.1

Experimental Properties

  • Color/Form: White powder
  • Density: 1.3399 (rough estimate)
  • Melting Point: 180 oC
  • Boiling Point: 487.8°C at 760 mmHg
  • Flash Point: 248.8±30.4 °C
  • Refractive Index: 1.6390 (estimate)
  • PSA: 152.34000
  • LogP: 2.23210
  • Solubility: Not determined
  • Vapor Pressure: 0.0±1.3 mmHg at 25°C

(2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid Security Information

(2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid Customs Data

  • HS CODE：2934100090
  • Customs Data：

    China Customs Code:

    2934100090

    Overview:

    2934100090. Compounds that structurally contain a non fused thiazole ring(Whether hydrogenated or not). VAT:17.0%. Tax refund rate:9.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934100090 other compounds containing an unfused thiazole ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

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(2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Dimethyl sulfoxide ;  20 h, 45 °C
2.1 Reagents: Sodium hydroxide Solvents: Methanol ;  6 h, 50 - 60 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  rt
Reference
Synthesis of side chain of ceftazidime activated thioester
Fu, Decai; et al, Zhongguo Yiyao Gongye Zazhi, 2002, 33(11), 523-524

Production Method 2

Reaction Conditions
1.1 Reagents: Hydrogen peroxide
Reference
Studies on condensed-heterocyclic azolium cephalosporins. I. Synthesis and antibacterial activity of 7β-[2-(2-aminothiazol-4-yl)-2(Z)-alkoxyiminoacetamido]-3-(imidazo[1,2-a]pyridinium-1-yl)methyl-3-cephem-4-carboxylates
Nishimura, Tatsuo; et al, Journal of Antibiotics, 1991, 44(12), 1371-93

Production Method 3

Reaction Conditions
1.1 -
2.1 Reagents: Hydrogen peroxide
Reference
Studies on condensed-heterocyclic azolium cephalosporins. I. Synthesis and antibacterial activity of 7β-[2-(2-aminothiazol-4-yl)-2(Z)-alkoxyiminoacetamido]-3-(imidazo[1,2-a]pyridinium-1-yl)methyl-3-cephem-4-carboxylates
Nishimura, Tatsuo; et al, Journal of Antibiotics, 1991, 44(12), 1371-93

(2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid Raw materials

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(2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid Related Literature

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Additional information on (2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid

Latest Research Insights on (2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid (CAS: 86299-47-0)

The compound (2Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxy-1,1-dimethyl-2-oxo-ethoxy)imino-acetic acid (CAS: 86299-47-0) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This β-lactamase inhibitor intermediate plays a crucial role in the synthesis of advanced antibiotic adjuvants, particularly in combating multidrug-resistant bacterial infections. Recent studies have focused on optimizing its synthetic pathways, evaluating its biochemical properties, and exploring its potential applications in combination therapies.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated enhanced synthetic yields (up to 78%) of this intermediate via a novel palladium-catalyzed coupling method, addressing previous challenges in stereochemical purity. Concurrently, crystallographic analysis revealed its unique binding conformation with class A β-lactamases, explaining its potent inhibitory effects observed in in vitro assays against ESBL-producing E. coli (IC50 = 0.8 μM).

Industry reports from Q2 2024 highlight its incorporation into next-generation β-lactam/β-lactamase inhibitor combinations, with Phase I clinical trials showing promising pharmacokinetic profiles when paired with ceftazidime. The tert-butoxy protective group in its structure has been identified as critical for maintaining stability during systemic circulation while allowing efficient enzymatic cleavage at target sites.

Emerging research directions include structural derivatization to improve blood-brain barrier penetration for CNS infections, as presented at the 2024 ACS Spring Meeting. Computational modeling studies suggest that modifications at the thiazole ring could enhance binding affinity against class D carbapenemases without compromising the compound's favorable toxicity profile (current LD50 > 2000 mg/kg in murine models).

Manufacturing advancements have been achieved through continuous flow chemistry approaches, reducing production costs by 40% compared to batch processes, as detailed in a recent Organic Process Research & Development publication. Regulatory filings indicate that the compound's synthesis now meets ICH Q11 standards, facilitating its adoption in commercial-scale antibiotic production.

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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:86299-47-0)頭孢他定側(cè)鏈酸
LE2469152
Purity:99%
Quantity:25KG,200KG,1000KG
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