N²-[3S-(3,5-dichlorophenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Base Information

• Chemical Name: N²-[3S-(3,5-dichlorophenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide
• CAS No.: 198421-52-2
• Molecular Formula: C₂₁H₃₀Cl₂N₂O₄S
• Molecular Weight: 477.452

Synonyms:N²-[3S-(3,5-dichlorophenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Chemical Property of N²-[3S-(3,5-dichlorophenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

Chemical Property:

Purity/Quality:

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Technology Process of N²-[3S-(3,5-dichlorophenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

There total 5 articles about N²-[3S-(3,5-dichlorophenylthio)-4-hydroxy-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: 87.0%

N2-[4-tert-butyloxy-3S-(3,5-dichlorophenylthio)-2S-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (198421-55-5) → N2-[3S-(3,5-dichlorophenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (198421-52-2)

Guidance literature:

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

DOI:10.1021/jm990377j

Reference yield:

1,2-bis(3,5-dichlorophenyl)disulfane (137897-99-5) → N2-[3S-(3,5-dichlorophenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (198421-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran; hexane / -78 °C

1.2: 36 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 77 percent / HOBT; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; DMAP / dimethylformamide / 20 °C

3.1: 87 percent / TFA / CH₂Cl₂ / 18 h / 0 °C

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Condensation / 2.1: Condensation / 3.1: acidolysis;

DOI:10.1021/jm990377j

Reference yield:

(S)-2-amino-N,3,3-trimethylbutanamide (89226-12-0) → N2-[3S-(3,5-dichlorophenylthio)-4-hydroxy-2S-isobutylsuccinyl]-L-tert-leucine-N1-methylamide (198421-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / HOBT; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; DMAP / dimethylformamide / 20 °C

2: 87 percent / TFA / CH₂Cl₂ / 18 h / 0 °C

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: acidolysis;

DOI:10.1021/jm990377j

upstream raw materials:

N²-[4-tert-butyloxy-3S-(3,5-dichlorophenylthio)-2S-isobutylsuccinyl]-L-tert-leucine-N¹-methylamide

1,2-bis(3,5-dichlorophenyl)disulfane

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

(R)-2-(2-(tert-butoxy)-2-oxoethyl)-4-methylpentanoic acid

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