methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate

Base Information

• Chemical Name: methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate
• CAS No.: 936712-97-9
• Molecular Formula: C₃₉H₄₄N₄O₉
• Molecular Weight: 712.8

Synonyms:

Chemical Property of methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate

There total 10 articles about methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate 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:

methyl 4-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}butanoate (1207955-33-6) + N-phthaloylglycine anhydride (6780-48-9) → methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate (936712-97-9)

Guidance literature:

methyl 4-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}butanoate; With trifluoroacetic acid; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

N-phthaloylglycine anhydride; With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jm3016848

Reference yield:

(2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine (858367-23-4) → methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate (936712-97-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide; water / 1,2-dimethoxyethane / 3 h / 0 °C

2.1: N,N-dimethyl-formamide / Inert atmosphere; Cooling with ice

2.2: 16 h / 0 - 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / N,N-dimethyl-formamide / 5 h / 20 °C

3.2: 48 h / 20 °C / Inert atmosphere

With water; trifluoroacetic acid; lithium hydroxide; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jm3016848

Reference yield:

(2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxylic acid (858367-12-1) → methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate (936712-97-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide / Inert atmosphere; Cooling with ice

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / N,N-dimethyl-formamide / 5 h / 20 °C

2.2: 48 h / 20 °C / Inert atmosphere

With trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm3016848

upstream raw materials:

(2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine

(2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxylic acid

methyl 4-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}butanoate

N-phthaloylglycine anhydride

Downstream raw materials:

5-[(2S,3R,4S,5S)-1-(2-aminoacetyl)-3-[(2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylprolylamino]butanoic acid

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