(S)-2-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; hydrochloride

Base Information

• Chemical Name: (S)-2-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; hydrochloride
• CAS No.: 83283-50-5
• Molecular Formula: C₂₁H₂₉N₅O₄*ClH
• Molecular Weight: 451.953
• Mol file: 83283-50-5.mol

Synonyms:

Chemical Property of (S)-2-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; hydrochloride

There total 5 articles about (S)-2-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; 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:

Z(OMe)-Ile-Gly-His-OBzl (83283-37-8) → (S)-2-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; hydrochloride (83283-50-5)

Guidance literature:

With hydrogenchloride; TFA-anisole; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1248/cpb.30.2595

Reference yield:

L-histidine benzyl ester (46921-20-4) → (S)-2-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; hydrochloride (83283-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 53.3 percent / DCC / tetrahydrofuran; dimethylformamide / 18 h

2: 1.) TFA-anisole, 2.) 3.2N HCl / diethyl ether / 1 h / 0 °C

With hydrogenchloride; TFA-anisole; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1248/cpb.30.2595

Reference yield:

Z(OMe)-Ile-OH (47174-55-0) → (S)-2-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; hydrochloride (83283-50-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 46.5 percent / DCC / tetrahydrofuran / 18 h

2: 62.5 percent / 1N NaOH / acetone / 0.5 h

3: 53.3 percent / DCC / tetrahydrofuran; dimethylformamide / 18 h

4: 1.) TFA-anisole, 2.) 3.2N HCl / diethyl ether / 1 h / 0 °C

With hydrogenchloride; sodium hydroxide; TFA-anisole; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.30.2595

upstream raw materials:

Z(OMe)-Ile-Gly-His-OBzl

L-histidine benzyl ester

Z(OMe)-Ile-OH

Z(OMe)-Ile-Gly-OH

Downstream raw materials:

(S)-2-[2-((2S,3S)-2-{[(S)-1-((S)-2-Amino-6-benzyloxycarbonylamino-hexanoyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-acetylamino]-3-(1H-imidazol-4-yl)-propionic acid benzyl ester; hydrochloride