6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: 6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 62166-87-4
• Molecular Formula: C₂₃H₂₇Cl₃N₂O₆S₂
• Molecular Weight: 597.968
• Mol file: 62166-87-4.mol

Synonyms:6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester

Chemical Property of 6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester

There total 3 articles about 6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl 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:

2-(tert-butoxycarbonylamino)-2-phenylacetic acid (2900-27-8,3601-66-9,14675-97-9,33125-05-2) + 6β-mercapto-penicillanic acid 2,2,2-trichloro-ethyl ester (62166-85-2) → 6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester (62166-87-4)

Guidance literature:

With pyridine; diisopropyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo00433a007

Reference yield:

6β-chloroacetylsulfanyl-penicillanic acid 2,2,2-trichloro-ethyl ester (62166-83-0) → 6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester (62166-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / -78 °C

2: diisopropylcarbodiimide, Py / CH₂Cl₂

With pyridine; sodium methylate; diisopropyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1021/jo00433a007

Reference yield:

(2S,5R)-6-Diazo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester (51056-24-7) → 6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester (62166-87-4)

Guidance literature:

Multi-step reaction with 3 steps

1: CCl₄ / Irradiation

2: NaOMe / methanol / -78 °C

3: diisopropylcarbodiimide, Py / CH₂Cl₂

With pyridine; sodium methylate; diisopropyl-carbodiimide; In methanol; tetrachloromethane; dichloromethane;

DOI:10.1021/jo00433a007

upstream raw materials:

2-(tert-butoxycarbonylamino)-2-phenylacetic acid

6β-mercapto-penicillanic acid 2,2,2-trichloro-ethyl ester

6β-chloroacetylsulfanyl-penicillanic acid 2,2,2-trichloro-ethyl ester

(2S,5R)-6-Diazo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester