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Sodium cyanoborohydride → 1-[N-(1-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline

HRID 1463023
ノート
印刷プレビュー

反応式

HRID 1463023 の反応式
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][C@@H:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].O=[C:22]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C([BH3-])#N.[Na+]>C(O)C>[CH2:26]([O:25][C:23]([CH:22]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][C@@H:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:24])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 18370473Benzyl 2-oxo-4-phenylbutanoateHCID 228271961-(L-alanyl)-4-(S)-(phenylthio)-L-proline

生成物 1

HCID 228272001-[N-(1-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 200 mg. of 1-(L-alanyl)-4-(S)-(phenylthio)-L-proline and 1.1 grams of benzyl 2-oxo-4-phenylbutyrate in 8 ml. of ethanol is stored at room temperature with 3 grams of powdered molecular sieves (type 4A). Over the course of three hours, 75 mg. of sodium cyanoborohydride is added. The reaction mixture is filtered and concentrated under reduced pressure. The residue is purified by absorption on a strong cation exchange resin and elution with 2% pyridine in water. After passage through a gel filtration column, the desired product, 1-[N-(1-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline, is obtained as a mixture of isomers that can be separated by high performance liquid chromatography.

後処理

  1. customOver the course of three hours, 75 mg
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by absorption on a strong cation exchange resin and elution with 2% pyridine in water
  5. filtrationAfter passage through a gel filtration column

出典と根拠

ORDレコード
ord-a15ab7189b69413a991b13aa19ad5748
出典データセット
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04462943

反応ノート

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