Ethanol → N-(1(S)-benzoyloxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline

HRID 2418428노트

반응식

HRID 2418428 반응식
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].O=[C:15]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C([BH3-])#N.[Na+].C([OH:40])C>>[C:19]([O:18][C:16]([C@@H:15]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:17])(=[O:40])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 4

HCID 702EthanolHCID 83525L-Alanyl-L-prolineHCID 5003444Sodium cyanoborohydrideHCID 18370473Benzyl 2-oxo-4-phenylbutanoate

생성물 1

HCID 22827631N-(1(S)-benzoyloxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline

실험 절차

A solution of L-alanyl-L-proline (167 mg) and benzyl 2-oxo-4-phenylbutyrate (1.20 g) in 5 ml of ethanol is stirred at room temperature with 3 g of powdered molecular sieves, type 4A. Sodium cyanoborohydride (75 mg) is then added in portions over the course of three hours. The product is purified by absorption on strong cation exchange resin and elution with 2% pyridine in water. After passage through a gel filtration (LH-20) column 220 mg of N-(1-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline is obtained as a mixture of isomers. Thin layer chromatography on silica gel eluted with 1 EtOAc, 1 n-butanol, 1 H2O, 1 HOAc shows one main spot, Rf 0.71. Isomers are separated using reverse phase HPLC to yield N-(1(S)-benzoyloxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline.

후처리

  1. customThe product is purified by absorption on strong cation exchange resin and elution with 2% pyridine in water
  2. filtrationAfter passage through a gel filtration (LH-20) column 220 mg of N-(1-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline
  3. customis obtained as a mixture of isomers
  4. washThin layer chromatography on silica gel eluted with 1 EtOAc, 1 n-butanol, 1 H2O, 1 HOAc
  5. customIsomers are separated

출처 및 근거

ORD 기록
ord-733d63ee2a844435bad722140e2bd443
출처 데이터셋
uspto-grants-1984_09
특허 번호
US04472380

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