(2R)-N¹-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N⁴-hydroxy-2-isobutyl-3-methylenesuccinamide

Base Information

• Chemical Name: (2R)-N¹-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N⁴-hydroxy-2-isobutyl-3-methylenesuccinamide
• CAS No.: 908350-12-9
• Molecular Formula: C₁₉H₂₇N₃O₄
• Molecular Weight: 361.441

Synonyms:(2R)-N¹-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N⁴-hydroxy-2-isobutyl-3-methylenesuccinamide

Chemical Property of (2R)-N¹-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N⁴-hydroxy-2-isobutyl-3-methylenesuccinamide

Chemical Property:

Purity/Quality:

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Technology Process of (2R)-N¹-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N⁴-hydroxy-2-isobutyl-3-methylenesuccinamide

There total 5 articles about (2R)-N¹-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N⁴-hydroxy-2-isobutyl-3-methylenesuccinamide 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: 82.0%

(3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid (198409-67-5) → (2R)-N1-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N4-hydroxy-2-isobutyl-3-methylenesuccinamide (908350-12-9)

Guidance literature:

(3R)-3-[(1S)-1-(methylcarbamoyl)-2-phenylethylcarbamoyl]-5-methyl-2-methylenehexanoic acid; With 1,3,5-trichloro-2,4,6-triazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 1h;

With hydroxylamine hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo060058h

Reference yield:

L-phenylalanine methylamide (35373-92-3) → (2R)-N1-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N4-hydroxy-2-isobutyl-3-methylenesuccinamide (908350-12-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2.9 g / hydroxybenzotriazole; EDCI / dimethylformamide / 20 °C

2.1: 77 percent / trifluoroacetic acid / CH₂Cl₂ / 10 h / 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,4,6-trichloro[1,3,5]triazine / dimethylformamide / 1 h

3.2: 82 percent / hydroxylamine hydrochloride; triethylamine / dimethylformamide / 2 h / 20 °C

With 1,3,5-trichloro-2,4,6-triazine; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo060058h

Reference yield:

(L)-phenylalanine ethyl ester hydrochloride (3182-93-2) → (2R)-N1-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-N4-hydroxy-2-isobutyl-3-methylenesuccinamide (908350-12-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran / 1 h

2.1: 2.9 g / hydroxybenzotriazole; EDCI / dimethylformamide / 20 °C

3.1: 77 percent / trifluoroacetic acid / CH₂Cl₂ / 10 h / 20 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,4,6-trichloro[1,3,5]triazine / dimethylformamide / 1 h

4.2: 82 percent / hydroxylamine hydrochloride; triethylamine / dimethylformamide / 2 h / 20 °C

With 1,3,5-trichloro-2,4,6-triazine; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo060058h

upstream raw materials:

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

L-phenylalanine methylamide

(L)-phenylalanine ethyl ester hydrochloride

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

Downstream raw materials:

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

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