Benzophenone imine → 2-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436502Notes

Reaction equation

HRID 1436502 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)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[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]([N:23]=[C:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[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 136809Benzophenone imineHCID 690155562-(R)-(2-(R)-amino-1-(S)-hydroxy-3-phenylpropyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866153742-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl esterYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-(R)-(2-(R)-amino-1-(S)-hydroxy-3-phenylpropyl)-piperazine-1-carboxylic acid tert-butyl ester (98 mg, 0.29 mmol) in dry dichloromethane and add benzophenoneimine (0.083 ml, 0.49 mmol) by syringe, stir overnight, and purify (silica gel chromatography, eluting with ethyl acetate and 98:2 ethyl acetate:triethylamine) to obtain (144 mg, 95% yield) of the title compound (144 mg, 95%) as a colorless oil.

Workup

  1. custompurify
  2. wash(silica gel chromatography, eluting with ethyl acetate and 98:2 ethyl acetate:triethylamine)

Sources & evidence

ORD record
ord-0dec55a79ff04f539ac1e89bf81dcd9f
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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