Triethylamine → 4-Acetyl-2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436503Notes

Reaction equation

HRID 1436503 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:37])[C@H:15]([N:23]=[C:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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:38](N1C=CN=C1)(=[O:40])[CH3:39].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:38](=[O:40])[CH3:39])[CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 866153742-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866153754-Acetyl-2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester (144 mg, 0.29 mmol)) in dry dichloromethane (3 mL). Add 1-acetylimidazole (48 mg, 0.43 mmol) and triethylamine (0.081 mL, 0.58 mmol) and stir for 2 h. Dilute with ethyl acetate and wash with 1 N HCl and saturated aqueous sodium bicarbonate, dry (magnesium sulfate), and concentrate to give the title compound which is used in the next step without further purification.

Workup

  1. washwash with 1 N HCl and saturated aqueous sodium bicarbonate
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-9c073de7d3a8461c89eee252b0cd55c0
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…