N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester

Base Information

• Chemical Name: N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester
• CAS No.: 124492-03-1
• Molecular Formula: C₂₂H₂₄N₂O₃S₂
• Molecular Weight: 428.576
• Mol file: 124492-03-1.mol

Synonyms:N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester

Chemical Property of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester

There total 1 articles about N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio 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: 40.0%

N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloride (114192-42-6) + 2-Mercaptobenzothiazole (149-30-4,118090-09-8) → N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester (124492-03-1)

Guidance literature:

With triethylamine; In dichloromethane; at -5 - 30 ℃; for 1h; Product distribution / selectivity;

Reference yield:

N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester (124492-03-1) → quinapril (85441-61-8,82768-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / CH₂Cl₂ / 4 h / -15 - -10 °C

2: hydrogen / Pd/C

With hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane;

DOI:10.1081/SCC-200048435

Reference yield:

benzyl (1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate (93779-31-8) + N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester (124492-03-1) → 2-Mercaptobenzothiazole (149-30-4,118090-09-8) + 2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester (87269-88-3,1356847-95-4,1356352-52-7)

Guidance literature:

With triethylamine; In dichloromethane; at -15 - -10 ℃; for 4h;

DOI:10.1081/SCC-200048435

upstream raw materials:

N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloride

2-Mercaptobenzothiazole

Downstream raw materials:

2-Mercaptobenzothiazole

2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester

quinapril benzyl ester

Ramipril