N²-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Base Information

• Chemical Name: N²-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide
• CAS No.: 198421-92-0
• Molecular Formula: C₂₉H₄₅N₃O₄S
• Molecular Weight: 531.76

Synonyms:N²-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Chemical Property of N²-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Chemical Property:

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Technology Process of N²-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

There total 1 articles about N²-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-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: 67.0%

(S)-2-amino-N,3,3-trimethylbutanamide (89226-12-0) + 3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylbutan-1,4-dioic acid 4-tert-butyl ester (198421-91-9) → N2-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (198421-92-0)

Guidance literature:

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm990377j

Reference yield: 99.0%

N2-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (198421-92-0) → N2-[3S-[3-(1-cyano-1-methylethyl)phenylthio]-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (198421-89-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 18h;

DOI:10.1021/jm990377j

Reference yield:

N2-[4-tert-butyloxy-3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (198421-92-0) → 2-[3-(cyano-dimethyl-methyl)-phenylsulfanyl]-N4-(2,2-dimethyl-1-methylcarbamoyl-propyl)-N1-hydroxy-3-isobutyl-succinamide

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / TFA / CH₂Cl₂ / 18 h / 0 °C

2.1: HOBT; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride / dimethylformamide / 20 °C

2.2: 40 percent / tBuMe₂SiONH₂; DMAP; 2,6-lutidine / dimethylformamide / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1.1: acidolysis / 2.1: Condensation / 2.2: Condensation;

DOI:10.1021/jm990377j

upstream raw materials:

(S)-2-amino-N,3,3-trimethylbutanamide

3S-[3-(1-cyano-1-methylethyl)phenylthio]-2S-isobutylbutan-1,4-dioic acid 4-tert-butyl ester

Downstream raw materials:

N²-[3S-[3-(1-cyano-1-methylethyl)phenylthio]-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

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