N²-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Base Information

• Chemical Name: N²-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide
• CAS No.: 204126-11-4
• Molecular Formula: C₂₅H₃₉Cl₂N₃O₆S
• Molecular Weight: 580.573

Synonyms:N²-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Chemical Property of N²-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Chemical Property:

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Technology Process of N²-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

There total 1 articles about N²-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide 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: 81.0%

3,5-dichlorobenzensulfonyl chloride (705-21-5) + (2S,3R)-2-Amino-3-((S)-2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-5-methyl-hexanoic acid tert-butyl ester → N2-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (204126-11-4)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃;

DOI:10.1021/jm990377j

Reference yield: 92.0%

N2-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (204126-11-4) → (2S,3R)-2-(3,5-Dichloro-benzenesulfonylamino)-3-((S)-2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-5-methyl-hexanoic acid (204126-10-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/jm990377j

Reference yield:

N2-[4-tert-butyloxy-3S-(3,5-dichlorobenzene-1-sulfonylamino)-2R-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (204126-11-4) → 2-(3,5-dichloro-benzenesulfonylamino)-N4-(2,2-dimethyl-1-methylcarbamoyl-propyl)-N1-hydroxy-3-isobutyl-succinamide

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / TFA / CH₂Cl₂ / 0 °C

2: 68 percent / tBuMe₂SiONH₂; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; 2,6-lutidine / dimethylformamide / 2 h / 20 °C

With 2,6-dimethylpyridine; O-(tert-butyldimethylsilanyl)hydroxylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: acidolysis / 2: Condensation;

DOI:10.1021/jm990377j

upstream raw materials:

3,5-dichlorobenzensulfonyl chloride

Downstream raw materials:

(2S,3R)-2-(3,5-Dichloro-benzenesulfonylamino)-3-((S)-2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-5-methyl-hexanoic acid

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