2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl ester

Base Information

• Chemical Name: 2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl ester
• CAS No.: 393157-42-1
• Molecular Formula: C₅₂H₅₂N₆O₁₂S₄
• Molecular Weight: 1081.28
• Mol file: 393157-42-1.mol

Synonyms:2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl ester

Chemical Property of 2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl ester

There total 6 articles about 2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl 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: 67.0%

2-(2-methylaminoacetylamino)benzoic acid methyl ester hydrochloride + (2S,4R)-4-[(3R,5S)-5-carboxy-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid (393153-91-8) → 2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl ester (393157-42-1)

Guidance literature:

With 4-methyl-morpholine; O-(2-oxo-1(2H)pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In dichloromethane; at 20 ℃;

DOI:10.1021/jm040857x

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl ester (393157-42-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hexamethyldisilazane / Heating

1.2: 82 percent / tetrahydrofuran / 16 h / 20 °C

2.1: 72 percent / dimethylformamide / 2.5 h / 100 °C

3.1: aq. LiOH / tetrahydrofuran / 1.5 h / 20 °C

4.1: 16.9 g / iodine; N,N-diisopropylethylamine / CH₂Cl₂

5.1: 67 percent / 4-methylmorpholine; O-(2-oxo-1(2H)pyridyl)-N,N,N',N'-tetramethyluronium*BF₄ / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; lithium hydroxide; O-(2-oxo-1(2H)pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; iodine; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm040857x

Reference yield:

2-Naphthalenesulfonyl chloride (93-11-8) → 2-[2-[[(2S,4R)-4-[(3R,5S)-5-[[(2-methoxycarbonylphenylcarbamoyl)methyl]methylcarbamoyl]-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carbonyl]methylamino]acetylamino]benzoic acid methyl ester (393157-42-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hexamethyldisilazane / Heating

1.2: 82 percent / tetrahydrofuran / 16 h / 20 °C

2.1: 72 percent / dimethylformamide / 2.5 h / 100 °C

3.1: aq. LiOH / tetrahydrofuran / 1.5 h / 20 °C

4.1: 16.9 g / iodine; N,N-diisopropylethylamine / CH₂Cl₂

5.1: 67 percent / 4-methylmorpholine; O-(2-oxo-1(2H)pyridyl)-N,N,N',N'-tetramethyluronium*BF₄ / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; lithium hydroxide; O-(2-oxo-1(2H)pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; iodine; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm040857x

upstream raw materials:

(2S,4R)-4-[(3R,5S)-5-carboxy-1-(naphthalene-2-sulfonyl)pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid

L-4-hydroxyproline methyl ester hydrochloride

2-Naphthalenesulfonyl chloride

(2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester