N^α-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-methylamide

Base Information

• Chemical Name: N^α-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-methylamide
• CAS No.: 458531-89-0
• Molecular Formula: C₃₇H₅₈N₆O₈S
• Molecular Weight: 746.969

Synonyms:N^α-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-methylamide

Chemical Property of N^α-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-methylamide

Chemical Property:

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Technology Process of N^α-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-methylamide

There total 7 articles about N^α-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-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: 40.0%

(S)-2-((S)-1-Ethoxycarbonyloxycarbonyl-3-methyl-butylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester + Thioacetic acid S-{2-amino-1-[(S)-3-methyl-1-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-ethyl} ester; hydrochloride → Nα-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-methylamide (458531-89-0)

Guidance literature:

With 4-methyl-morpholine; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1248/cpb.50.239

Reference yield:

(2S)-2-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carbonyl]amino}-4-methylpentanoic acid (68385-28-4) → Nα-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-methylamide (458531-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NMM

2: 40 percent / NMM / dimethylformamide / 1 h / 0 °C

With 4-methyl-morpholine; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.50.239

Reference yield:

Boc-Leu-Phe-NHMe → Nα-[3-(tert-butyloxycarbonyl-prolyl-leucyl-amino)-2(R,S)-(acetylsulfanyl)propionyl]-leucyl-phenylalanine N-methylamide (458531-89-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 4 N HCl / ethyl acetate

2: 86 percent / EDC; Et₃N; HOBt / dimethylformamide / 21 h / -3 - 0 °C

3: pyridine / CH₂Cl₂ / 2 h / 0 °C

4: dimethylformamide / 48 h / 20 °C

5: 100 percent / 4 N HCl / ethyl acetate

6: 40 percent / NMM / dimethylformamide / 1 h / 0 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.50.239

upstream raw materials:

(2S)-2-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carbonyl]amino}-4-methylpentanoic acid

{2-Hydroxy-2-[(S)-3-methyl-1-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

thioacetic acid S-{2-tert-butoxycarbonylamino-1-[3-methyl-1-(1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-ethyl} ester

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