Methanesulfonyl chloride → 3-(4(S)-benzyl-2-oxooxazolidin-3-yl)-1(R)-(3-benzyloxyphenyl)-2(S)-isopropoxy-3-oxopropyl methanesulfonate

HRID 1985386

반응식

HRID 1985386 반응식
[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[CH:15]([O:32][CH:33]([CH3:35])[CH3:34])[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:19]=1)[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:37][S:38]([O:17][C@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:19]=1)[C@H:15]([O:32][CH:33]([CH3:34])[CH3:35])[C:14]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:36])(=[O:40])=[O:39]

참가 물질

5

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 690085004-Benzyl-3-(3-(3-benzyloxyphenyl)-3-hydroxy-2-isopropoxy propionyl]oxazolidin-2-one

생성물 1

HCID 867608793-(4(S)-benzyl-2-oxooxazolidin-3-yl)-1(R)-(3-benzyloxyphenyl)-2(S)-isopropoxy-3-oxopropyl methanesulfonate

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

12.9 g of 4-Benzyl-3-(3-(3-benzyloxyphenyl)-3-hydroxy-2-isopropoxy propionyl]oxazolidin-2-one was dissolved in 30 ml of pyridine, and 3.06 ml of methanesulfonyl chloride was dropwise added thereto under ice-cooling. After stirring was continued at room temperature for 2 hours, the reaction solution was diluted with ethyl acetate and washed successively with 1N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated, to give 3-(4(S)-benzyl-2-oxooxazolidin-3-yl)-1(R)-(3-benzyloxyphenyl)-2(S)-isopropoxy-3-oxopropyl methanesulfonate. This product was then dissolved in 300 ml of ethanol, and 2 g of 10% palladium carbon was added, and the mixture was stirred overnight under hydrogen atmosphere at room temperature. The reaction solution was filtered, and the filtrate was concentrated. The residue was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate, The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 5.87 g of the title compound as a colorless oil in the 2:1→3:2 hexane-ethyl acetate fraction.

후처리

  1. temperatureunder ice-cooling
  2. washwashed successively with 1N hydrochloric acid and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent was concentrated

출처 및 근거

ORD 기록
ord-63b7579028004e8883e28aaf22426c36
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544835B2

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