(R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide

Base Information

• Chemical Name: (R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide
• CAS No.: 114457-27-1
• Molecular Formula: C₃₅H₅₃N₅O₆
• Molecular Weight: 639.836
• Mol file: 114457-27-1.mol

Synonyms:(R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide

Chemical Property of (R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide

There total 7 articles about (R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide 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: 43.0%

2(R)-2-<(4-morpholinylcarbonyl)methyl>-3-phenylpropionic acid (112804-14-5) + (S)-2-Amino-N-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-(1H-imidazol-4-yl)-propionamide; hydrochloride (104882-47-5) → (R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide (114457-27-1)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; 0 deg C, 2.5 h; 25 deg C, 12 h;

DOI:10.1021/jm00120a006

Reference yield:

(4S)-3-(3-phenylpropionyl)-4-(2-propyl)oxazolidin-2-one (95798-31-5) → (R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide (114457-27-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium hexamethyldisilylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

2: 94 percent / n-butyllithium / tetrahydrofuran / 1 h / 0 °C

3: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) N-methylmorpholine, isobutyl chloroformate / 1.) THF, 5 min, 2.) 1 h

5: 100 percent / hydrogen / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr

6: 43 percent / hydroxybenzotriazole, DCC / dimethylformamide / 0 deg C, 2.5 h; 25 deg C, 12 h

With 4-methyl-morpholine; n-butyllithium; hydrogen; sodium hexamethyldisilazane; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00120a006

Reference yield:

(3R)-3-Benzyloxycarbonyl-3-phenylmethylpropionic acid (116129-80-7) → (R)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-4-morpholin-4-yl-4-oxo-butyramide (114457-27-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate / 1.) THF, 5 min, 2.) 1 h

2: 100 percent / hydrogen / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr

3: 43 percent / hydroxybenzotriazole, DCC / dimethylformamide / 0 deg C, 2.5 h; 25 deg C, 12 h

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; isobutyl chloroformate; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00120a006

upstream raw materials:

2(R)-2-<(4-morpholinylcarbonyl)methyl>-3-phenylpropionic acid

(S)-2-Amino-N-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-(1H-imidazol-4-yl)-propionamide; hydrochloride

(4S)-3-(3-phenylpropionyl)-4-(2-propyl)oxazolidin-2-one

(3R)-3-Benzyloxycarbonyl-3-phenylmethylpropionic acid