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

HRID 1033854노트

반응식

HRID 1033854 반응식
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]

참가 물질

7

반응물 4

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

생성물 2

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-01fd583483854956ade5e9c9412fe177
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05312826

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