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Sodium borohydride → trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

HRID 2107500
ノート
印刷プレビュー

反応式

HRID 2107500 の反応式
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][O:8][C:9](=[O:29])[C@@H:10]2[CH2:14][C:13](=[O:15])[CH2:12][N:11]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:29])[C@@H:10]2[CH2:14][C@H:13]([OH:15])[CH2:12][N:11]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])=[CH:30][CH:31]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:29])[C@@H:10]2[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])=[CH:30][CH:31]=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 2

HCID 4311764Sodium borohydrideHCID 151163081-(p-nitrobenzyloxycarbonyl)-4-oxo-L-proline p-methoxybenzyl ester

生成物 2

HCID 13504318trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl esterHCID 13504319cis-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

650 mg of 1-(p-nitrobenzyloxycarbonyl)-4-oxo-L-proline p-methoxybenzyl ester was dissolved in 45 ml of ethanol, and 86 mg of sodium borohydride was added thereto in two divided portions at room temperature. After 30 minutes, the reaction mixture was concentrated under reduced pressure at 30° C. or below, and the concentrate was diluted with ethyl acetate, washed with water, dried over sodium sulfate and distilled off to remove the solvent. The residue was purified by silica gel column chromatography to obtain cis-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester (450 mg) and trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester (190 mg).

後処理

  1. customat room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure at 30° C. or below
  3. additionthe concentrate was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled off
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-be0bcb7a7be642588485a94d8c4b1ace
出典データセット
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04933333

反応ノート

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