L-Alanyl-L-proline → Enalaprilat Benzyl Ester

HRID 1758854ノート

反応式

HRID 1758854 の反応式
[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(O)C>[CH2:19]([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])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

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

生成物 1

HCID 22822716Enalaprilat Benzyl Ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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 post, Rf 0.71. Isomers are separated using reverse phase HPLC to yield N-(1(S)-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline.

後処理

  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

出典と根拠

ORDレコード
ord-d0de89bb7d8f491f8e70d67f4aba2352
出典データセット
uspto-grants-1983_02
特許番号
US04374829

反応ノート

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