(S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester

Base Information

• Chemical Name: (S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester
• CAS No.: 79974-09-7
• Molecular Formula: C₄₆H₄₅N₃O₁₀
• Molecular Weight: 799.877
• Mol file: 79974-09-7.mol

Synonyms:(S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester

Chemical Property of (S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester

There total 7 articles about (S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl 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:

L-aspartic acid dibenzyl ester hydrochloride (6327-59-9,174457-99-9) + (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester → (S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester (79974-09-7)

Guidance literature:

With triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide; at 25 ℃; for 2h; Yield given;

DOI:10.1021/jm00344a018

Reference yield:

N-methyl-p-aminobenzoic acid (10541-83-0,937737-33-2) → (S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester (79974-09-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / 2 N NaOH / dioxane; H₂O / 0.5 h / 0 - 5 °C

2: 99 percent / SOCl₂ / benzene / 2 h / Heating

3: 89 percent / (i-Pr)2NEt / dioxane; H₂O

4: Et₃N / dimethylformamide; dioxane / 1 h / -10 °C

5: Et₃N / dimethylformamide; dioxane / 2 h / 25 °C

With sodium hydroxide; thionyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00344a018

Reference yield:

1-benzyl L-glutamate (13030-09-6) → (S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester (79974-09-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / (i-Pr)2NEt / dioxane; H₂O

2: Et₃N / dimethylformamide; dioxane / 1 h / -10 °C

3: Et₃N / dimethylformamide; dioxane / 2 h / 25 °C

With triethylamine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00344a018

upstream raw materials:

L-aspartic acid dibenzyl ester hydrochloride

N-methyl-p-aminobenzoic acid

1-benzyl L-glutamate

4-<<(benzyloxy)carbonyl>methylamino>benzoic acid

Downstream raw materials:

methotrexate-γ-aspartate

Refernces