6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure

Base Information

• Chemical Name: 6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure
• CAS No.: 73974-15-9
• Molecular Formula: C₂₅H₃₃N₅O₈S
• Molecular Weight: 563.632
• Mol file: 73974-15-9.mol

Synonyms:6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure

Chemical Property of 6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure

There total 4 articles about 6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure 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:

L-alanyl-alanine methylester hydrochloride (41036-19-5,105328-90-3) → 6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure (73974-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / NEM, DCCI / CH₂Cl₂; dimethylformamide / 20 h / 0 °C

2: 85 percent / 1) 1 N NaOH / methanol / 2 h / Ambient temperature

3: 1) NMM, Chlorkohlensaeure-isobutylester / 1) THF, 10 min, -20 to -15 deg C, 1) 0 deg C, 2 h

With 4-methyl-morpholine; N-Ethylmaleimide; sodium hydroxide; dicyclohexyl-carbodiimide; isobutyl chloroformate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/jlac.198019800105

Reference yield:

(S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate (19794-10-6,51513-86-1,59602-19-6,71257-75-5,71257-76-6) → 6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure (73974-15-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / 1.2 N HCl / acetic acid / 0.42 h

2: 85 percent / NEM, DCCI / CH₂Cl₂; dimethylformamide / 20 h / 0 °C

3: 85 percent / 1) 1 N NaOH / methanol / 2 h / Ambient temperature

4: 1) NMM, Chlorkohlensaeure-isobutylester / 1) THF, 10 min, -20 to -15 deg C, 1) 0 deg C, 2 h

With 4-methyl-morpholine; hydrogenchloride; N-Ethylmaleimide; sodium hydroxide; dicyclohexyl-carbodiimide; isobutyl chloroformate; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/jlac.198019800105

Reference yield:

N-[(benzyloxy)carbonyl]-L-alanyl-L-alanyl-L-alanine methyl ester (3057-69-0) → 6-(Benzyloxycarbonyl-alanyl-alanyl-alanylamino)penicillansaeure (73974-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 1) 1 N NaOH / methanol / 2 h / Ambient temperature

2: 1) NMM, Chlorkohlensaeure-isobutylester / 1) THF, 10 min, -20 to -15 deg C, 1) 0 deg C, 2 h

With 4-methyl-morpholine; sodium hydroxide; isobutyl chloroformate; In methanol;

DOI:10.1002/jlac.198019800105

upstream raw materials:

N^α-benzyloxycarbobyl-L-alanyl-L-alanyl-L-alanine

6β-amino-penicillanic acid; potassium salt

(S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate

N-[(benzyloxy)carbonyl]-L-alanyl-L-alanyl-L-alanine methyl ester