Trityl chloride → (S)-ethyl 3-hydroxy-4-trityloxybutanoate

HRID 1168053ノート

反応式

HRID 1168053 の反応式
[OH:1][C@H:2]([CH2:9][OH:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[OH:1][C@H:2]([CH2:9][O:10][C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

参加物

6

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 10855622(S)-ethyl 3,4-dihydroxybutanoate

生成物 1

HCID 10883658(S)-ethyl 3-hydroxy-4-trityloxybutanoate収率 31%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To (S)-ethyl 3,4-dihydroxybutanoate (1.40 g, 9.45 mmol) in methylene chloride (20 ml) were added triethylamine (1.15 g, 11.36 mmol) and DMAP (17 mg, 0.139 mmol) and the solution was cooled in ice bath. Trityl chloride (2.90 g, 10.4 mol) in methylene chloride (15 ml) was dropped to the solution under stirring and then stirred at room temperature over night. The reaction mixture was washed with saturated ammonium chloride and then saturated brine, dried on magnesium sulfate, filtered and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-ethyl 3-hydroxy-4-trityloxybutanoate (1.11 g, yield 31%).

後処理

  1. temperaturethe solution was cooled in ice bath
  2. stirringstirred at room temperature over night
  3. washThe reaction mixture was washed with saturated ammonium chloride
  4. dry with materialsaturated brine, dried on magnesium sulfate
  5. filtrationfiltered
  6. customcondensed in vacuo

出典と根拠

ORDレコード
ord-abdd119dbf614fadb375c09ec1071e2a
出典データセット
uspto-grants-2003_09
特許番号
US06620977B1

反応ノート

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