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

HRID 1463023
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HRID 1463023 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a15ab7189b69413a991b13aa19ad5748
출처 데이터셋
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04462943

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