Potassium Carbonate → N-((1R)-1-benzyloxycarbonyl-3-phenylpropyl)-(L)-phenylalanine tert-butyl ester

HRID 1033854Notes

Reaction equation

HRID 1033854 reaction equation
Br[CH:2]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[C:21]([O:25][C:26](=[O:36])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH2:28])([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].CN(C)P(=O)(N(C)C)N(C)C>C(OCC)(=O)C>[C:21]([O:25][C:26](=[O:36])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:28][C@H:2]([C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:24])([CH3:22])[CH3:23].[C:21]([O:25][C:26](=[O:36])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:28][C@@H:2]([C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateHCID 19024556Benzyl 2-bromo-4-phenylbutyrate

Product 2

HCID 53980259N-((1R)-1-benzyloxycarbonyl-3-phenylpropyl)-(L)-phenylalanine tert-butyl esterHCID 57290041N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)-(L)-phenylalanine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 33 g of benzyl 2-bromo-4-phenylbutyrate, 22.1 g of (L)-phenylalanine tert-butyl ester, 13.8 g of potassium carbonate and 30 ml of hexamethylphosphoric triamide was stirred at room temperature overnight. Then, ethyl acetate was added to the mixture, and the insolubles were removed by filtration. The filtrate was washed and dried, and then the solvent was removed. The residue was purified by silica gel to obtain 16.6 g of N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)-(L)-phenylalanine tert-butyl ester and 9.9 g of N-((1R)-1-benzyloxycarbonyl-3-phenylpropyl)-(L)-phenylalanine tert-butyl ester as oily products, respectively.

Workup

  1. customthe insolubles were removed by filtration
  2. washThe filtrate was washed
  3. customdried
  4. customthe solvent was removed
  5. customThe residue was purified by silica gel

Sources & evidence

ORD record
ord-01fd583483854956ade5e9c9412fe177
Source dataset
uspto-grants-1994_05
Patent number
US05312826

Reaction notes

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