Methanesulfonyl chloride → 2,2-dichloro-1-((4S,5R)-5-(4-(6-(chloromethyl)pyridin-3-yl)phenyl)-4 (fluoromethyl)-2,2-dimethyloxazolidin-3-yl)ethanone

HRID 1500274

반응식

HRID 1500274 반응식
[Cl:1][CH:2]([Cl:28])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][C:21]([CH2:24]O)=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:27])[CH3:26])=[O:4].CCN(C(C)C)C(C)C.CS([Cl:42])(=O)=O>C(Cl)Cl>[Cl:28][CH:2]([Cl:1])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][C:21]([CH2:24][Cl:42])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:26])[CH3:27])=[O:4]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 866954062,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-(6-(hydroxymethyl)pyridin-3-yl)phenyl)-2,2-dimethyloxazolidin-3-yl)ethanone

생성물 1

HCID 867131642,2-dichloro-1-((4S,5R)-5-(4-(6-(chloromethyl)pyridin-3-yl)phenyl)-4 (fluoromethyl)-2,2-dimethyloxazolidin-3-yl)ethanone수율 97.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a cooled (ice-water) solution of the product of step 1 (800 mg, 1.87 mmol) and DIPEA (0.675 mL, 3.75 mmol) in DCM (10 mL) is slowly added methanesulfonyl chloride (0.150 mL, 1.87 mmol). The reaction mixture is stirred at room temperature for 6 hours. The reaction is diluted with DCM (10 mL), washed with water (2×10 mL) dried over Na2SO4 and concentrated under reduced pressure to give the title compound (813 mg): LCMS m/z (Cl): 445 [M+H].

후처리

  1. washwashed with water (2×10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-63de992dc7ad49eea645a79efe833794
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206126B2

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