(-)-tert-butyl 3-aminonocardicinate hydrochloride

Base Information

• Chemical Name: (-)-tert-butyl 3-aminonocardicinate hydrochloride
• CAS No.: 123004-73-9
• Molecular Formula: C₁₅H₂₀N₂O₄*ClH
• Molecular Weight: 328.796
• Mol file: 123004-73-9.mol

Synonyms:(-)-tert-butyl 3-aminonocardicinate hydrochloride

Chemical Property of (-)-tert-butyl 3-aminonocardicinate hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-tert-butyl 3-aminonocardicinate hydrochloride

There total 5 articles about (-)-tert-butyl 3-aminonocardicinate hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester (110207-46-0) → (-)-tert-butyl 3-aminonocardicinate hydrochloride (123004-73-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; for 48h; under 2585.7 Torr;

DOI:10.1016/S0040-4039(00)83888-5

Reference yield:

tert-butyl N-(4,5-diphenyl-4-oxazolin-2-onyl)-L-seryl-D-glycinate (111216-46-7) → (-)-tert-butyl 3-aminonocardicinate hydrochloride (123004-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent

2: 94 percent / H₂,HCl / 10percent Pd/C / 48 h / 2585.7 Torr

With hydrogenchloride; hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(00)83888-5

Reference yield:

L-Ox-serine dicyclohexylammonium salt → (-)-tert-butyl 3-aminonocardicinate hydrochloride (123004-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / hydroxybenzotriazole monohydrate, dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 1.) 0 deg C, 2.5 h, 2.) RT, 1.5 h

2: 84 percent / triethyl phosphite, diethyl azodicarboxylate / tetrahydrofuran / 4.5 h

3: 89 percent / 1N HCl / Pd/C / ethyl acetate; methanol; acetic acid / 44 h / 2068.6 Torr

With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; diethylazodicarboxylate; triethyl phosphite; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00158a040

upstream raw materials:

(-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester

tert-butyl N-(4,5-diphenyl-4-oxazolin-2-onyl)-L-seryl-D-glycinate

D-glycine tert-butyl ester toluenesulfonate salt

Downstream raw materials:

(R)-{(S)-3-[(R)-2-tert-Butoxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-oxo-azetidin-1-yl}-(4-hydroxy-phenyl)-acetic acid tert-butyl ester

di-tert-butyl N-(tert-butoxycarbonyl)nocardicin D

(R)-2-tert-Butoxycarbonylamino-4-[4-((R)-tert-butoxycarbonylamino-{(S)-1-[(R)-tert-butoxycarbonyl-(4-hydroxy-phenyl)-methyl]-2-oxo-azetidin-3-ylcarbamoyl}-methyl)-phenoxy]-butyric acid tert-butyl ester

(R)-4-[4-((R)-Benzyloxycarbonylamino-{(S)-1-[(R)-tert-butoxycarbonyl-(4-hydroxy-phenyl)-methyl]-2-oxo-azetidin-3-ylcarbamoyl}-methyl)-phenoxy]-2-tert-butoxycarbonylamino-butyric acid tert-butyl ester