(-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide

Base Information

• Chemical Name: (-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide
• CAS No.: 540744-17-0
• Molecular Formula: C₂₇H₃₁N₃O₅S₂
• Molecular Weight: 541.692

Synonyms:(-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide

Chemical Property of (-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide

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Technology Process of (-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide

There total 2 articles about (-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide 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:

(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-3-phenylpropanoic acid (357417-35-7) → (-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide (540744-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / DMF / 2 h / 20 °C

2: 3.95 g / Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

With thionyl chloride; triethylamine; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1002/hlca.200390046

Reference yield:

(S)-3-{[(4-methylphenyl)sulfonyl]amino}-3-phenylpropanoic acid chloride + N-[(2E)-4-aminobut-2-enyl]-4-methylbenzenesulfonamide*CF3COOH → (-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide (540744-17-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1002/hlca.200390046

Reference yield: 49.0%

1,3-dimesyloxypropane (15886-84-7) + (-)-(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-N-{(2E)-4-{[(4-methylphenyl)sulfonyl]amino}but-2-enyl}3-phenylpropanamide (540744-17-0) → (E)-3-Phenyl-N-((E)-4-{(toluene-4-sulfonyl)-[3-(toluene-4-sulfonylamino)-propyl]-amino}-but-2-enyl)-acrylamide + (+)-(4S,11E)-5,9-bis[(4-methylphenyl)sulfonyl]-4-phenyl-1,5,9-triazacyclotridec-11-en-2-one (540744-18-1)

Guidance literature:

caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 120h;

DOI:10.1002/hlca.200390046

upstream raw materials:

(3S)-3-{[(4-methylphenyl)sulfonyl]amino}-3-phenylpropanoic acid

Downstream raw materials:

(+)-(4S,11E)-5,9-bis[(4-methylphenyl)sulfonyl]-4-phenyl-1,5,9-triazacyclotridec-11-en-2-one

(+)-(4S,11E)-4-phenyl-1,5,9-triazacyclotridec-11-en-2-one

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