N-Acetyl-N-[2-(trifluoromethyl)phenyl]acetamide → 2-(R)-(2-(R)-Acetylamino-1-(S)-hydroxy-3-phenyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436511Notes

Reaction equation

HRID 1436511 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C@@H:14]([OH:24])[C@H:15]([NH2:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](N(C1C=CC=CC=1C(F)(F)F)C(=O)C)(=[O:27])[CH3:26]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C@@H:14]([OH:24])[C@H:15]([NH:23][C:25](=[O:27])[CH3:26])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11064662N-Acetyl-N-[2-(trifluoromethyl)phenyl]acetamideHCID 690155562-(R)-(2-(R)-amino-1-(S)-hydroxy-3-phenylpropyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 690153032-(R)-(2-(R)-Acetylamino-1-(S)-hydroxy-3-phenyl-propyl)-piperazine-1-carboxylic acid tert-butyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-(R)-(2-(R)-amino-1-(S)-hydroxy-3-phenyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester (232 mg, 0.69 mmol) in 7 ml of dry CH2Cl2 and add N-acetyl-N-(2-trifluoromethyl-phenyl)-acetamide (Tetrahedron Letters, 38(21), 3751 (1997)) (162 mg, 0.66 mmol). Stir at room temperature overnight. Subject reaction mixture to silica gel chromatography, eluting ethyl acetate/triethylamine 98:2 to obtain 122 mg of the title compound (60% yield based on 79% conversion) and 50 mg of starting amine.

Workup

  1. customreaction mixture to silica gel chromatography
  2. washeluting ethyl acetate/triethylamine 98:2

Sources & evidence

ORD record
ord-4d7e3747bffe443aaa88dc6523c70435
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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