methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate

Base Information

• Chemical Name: methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate
• CAS No.: 936712-91-3
• Molecular Formula: C₃₁H₄₃N₃O₆
• Molecular Weight: 553.699
• Mol file: 936712-91-3.mol

Synonyms:methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate

Chemical Property of methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate

There total 9 articles about methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate 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:

(2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxylic acid (858367-12-1) + methyl 6-aminocaproate hydrochloride (1926-80-3) → methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate (936712-91-3)

Guidance literature:

(2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxylic acid; methyl 6-aminocaproate hydrochloride; In N,N-dimethyl-formamide; Inert atmosphere; Cooling with ice;

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h; 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 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate (936712-91-3)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jm3016848

Reference yield:

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate (936712-91-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium nitrite; sulfuric acid / 24 h / 0 °C

2.1: toluene-4-sulfonic acid; 2,2-dimethoxy-propane / methanol / 24 h / 45 °C

2.2: 72 h / 20 °C

3.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 20 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0.25 h / 20 °C

4.2: 16 h / 20 °C

4.3: 2 h / -78 °C

5.1: triethylamine; silver(I) acetate / acetonitrile / 5 h / 20 °C

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

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

7.2: 16 h / 0 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sulfuric acid; water; silver(I) acetate; toluene-4-sulfonic acid; triethylamine; 2,2-dimethoxy-propane; lithium hydroxide; sodium nitrite; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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 6-aminocaproate hydrochloride

L-isoleucine

Downstream raw materials:

6-{(2S,3R,4S,5S)-3-[(2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxamido}hexanoic acid