(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

Base Information

• Chemical Name: (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
• CAS No.: 110207-48-2
• Molecular Formula: C₂₈H₃₅N₃O₈
• Molecular Weight: 541.601
• Mol file: 110207-48-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 11 articles about (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 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: 67.0%

(-)-tert-butyl 3-aminonocardicinate hydrochloride (123004-73-9) → (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 (110207-48-2)

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/jo4007893

Reference yield: 59.0%

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine (27460-85-1) + (-)-tert-butyl 3-aminonocardicinate hydrochloride (123004-73-9) → (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 (110207-48-2)

Guidance literature:

With 2,6-dimethylpyridine; isobutyl chloroformate; In N,N-dimethyl-formamide; acetone; at -5 - 20 ℃; for 1.5h;

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

Reference yield:

(-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester (110207-46-0) → (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 (110207-48-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / H₂,HCl / 10percent Pd/C / 48 h / 2585.7 Torr

2: 59 percent / i-BuOCOCl/2,6-lutidine / acetone; dimethylformamide / 1.5 h / -5 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; hydrogen; isobutyl chloroformate; palladium on activated charcoal; In N,N-dimethyl-formamide; acetone;

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

upstream raw materials:

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine

(-)-tert-butyl 3-aminonocardicinate hydrochloride

(-)-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

Downstream raw materials:

nocardicin G-pantetheine trifluoroacetate

epi-nocardicin G-SNAC

nocardicin G-SNAC

N-(tert-butyloxycarbonyl)nocardicin G