4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid

Base Information

• Chemical Name: 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid
• CAS No.: 192052-58-7
• Molecular Formula: C₄₃H₅₅N₃O₁₃S
• Molecular Weight: 853.988
• Mol file: 192052-58-7.mol

Synonyms:

Chemical Property of 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid

There total 4 articles about 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid 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: 43.0%

(tert-butyl)dimethylsilyl 4-(chlorosulfonyl)benzoate (192052-57-6) + (S)-2-[(S)-2-((S)-4-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester (192052-54-3) → 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid (192052-58-7) + C49H69N3O13SSi

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 26h; Ambient temperature; 1.) -3 deg C;

DOI:10.1002/hlca.19970800304

Reference yield:

p-carboxyphenylsulfonyl chloride (10130-89-9) → 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid (192052-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (^tBu)Me₂SiCl / tetrahydrofuran / 0.33 h / 35 °C

2: 45 percent / (ⁱPr)Et₂N / CH₂Cl₂ / 26 h / Ambient temperature; 1.) -3 deg C

With tert-butyldimethylsilyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/hlca.19970800304

Reference yield:

(S)-5-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) 2-((tert-butoxycarbonyl)amino)pentanedioate (32886-55-8) → 4-{4-[(S)-2-((S)-1-Benzyloxycarbonyl-3-methyl-butylcarbamoyl)-2-((S)-4-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-ethyl]-phenoxysulfonyl}-benzoic acid (192052-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / (ⁱPr)2EtN / dimethylformamide / 23 h / Ambient temperature

2: 45 percent / (ⁱPr)Et₂N / CH₂Cl₂ / 26 h / Ambient temperature; 1.) -3 deg C

With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19970800304

upstream raw materials:

(tert-butyl)dimethylsilyl 4-(chlorosulfonyl)benzoate

(S)-2-[(S)-2-((S)-4-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester

p-carboxyphenylsulfonyl chloride

(S)-5-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) 2-((tert-butoxycarbonyl)amino)pentanedioate

Downstream raw materials:

C₅₆H₇₀N₈O₁₆S