(3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid

Base Information

• Chemical Name: (3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid
• CAS No.: 198409-67-5
• Molecular Formula: C₁₉H₂₆N₂O₄
• Molecular Weight: 346.426

Synonyms:(3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid

Chemical Property of (3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid

Chemical Property:

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Technology Process of (3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid

There total 4 articles about (3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic 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: 77.0%

(R)-tert-butyl 3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoate (908350-11-8) → (3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid (198409-67-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 10h;

DOI:10.1021/jo060058h

Reference yield:

L-phenylalanine methylamide (35373-92-3) → (3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid (198409-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.9 g / hydroxybenzotriazole; EDCI / dimethylformamide / 20 °C

2: 77 percent / trifluoroacetic acid / CH₂Cl₂ / 10 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo060058h

Reference yield:

(2R)-2-[1-(tert-butoxycarbonyl)vinyl]-4-methylpentanoic acid (145339-42-0) → (3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid (198409-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.9 g / hydroxybenzotriazole; EDCI / dimethylformamide / 20 °C

2: 77 percent / trifluoroacetic acid / CH₂Cl₂ / 10 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo060058h

upstream raw materials:

(R)-tert-butyl 3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoate

L-phenylalanine methylamide

(L)-phenylalanine ethyl ester hydrochloride

(2R)-2-[1-(tert-butoxycarbonyl)vinyl]-4-methylpentanoic acid

Downstream raw materials:

BB-94 acid

S-(2S,3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-2-(hydroxycarbamoyl)-5-methylhexyl ethanethioate

(2S,3R)-2-Mercaptomethyl-5-methyl-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid

2-[(2S,3R)-2-Hydroxycarbamoyl-5-methyl-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexylsulfanyl]-benzoic acid methyl ester

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