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

HRID 1168053노트

반응식

HRID 1168053 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-abdd119dbf614fadb375c09ec1071e2a
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620977B1

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