tert-Butyl methyl ether → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

HRID 531228노트

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HRID 531228 반응식
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([Br:26])=[CH:24][N:23]=[C:22](SC)[N:21]=3)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[S:32]([O-:37])(O[O-])(=O)=[O:33].[K+].[K+].[CH3:40]OC(C)(C)C>C(#N)C.O>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([Br:26])=[CH:24][N:23]=[C:22]([S:32]([CH3:40])(=[O:37])=[O:33])[N:21]=3)[C@H:14]2[CH3:29])[CH:4]=[C:3]([C:2]([F:1])([F:31])[F:30])[CH:8]=1

참가 물질

6

반응물 3

HCID 15413tert-Butyl methyl etherHCID 10313463Potassium peroxymonosulphateHCID 57576287(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one2회

생성물 1

HCID 86704625(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one수율 96%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

To a suspension of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfanyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 8, 10 g, 18.86 mmol) in acetonitrile (25 mL) and water (25 mL) was added potassium peroxymonosulfate (27.8 g, 45.3 mmol). After it was stirred at room for 14 hours, LCMS showed complete conversion of the starting material. It was distributed between water (200 mL) and t-butyl methyl ether (300 mL). The organic layer was washed with water (200 mL) and brine, dried over sodium sulfate, filtered and the filtrate concentrated to get the title compound (10.2 g, 96% yield) as a brightly white solid. LCMS (M+H)+: 564.05. 1H NMR (CDCl3, 500 MHz): δ 8.99 (s, 1H), 7.93 (s, 1H), 7.84 (s, 2H), 6.02 (d, 8.5 Hz, 1H), 5.14 (d, 18.5 Hz, 1H), 4.56 (m, 1H), 4.42 (d, 18.0 Hz, 1H), 3.37 (S, 3H), 0.86 (d, 6.5 Hz, 3H).

후처리

  1. washThe organic layer was washed with water (200 mL) and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

출처 및 근거

ORD 기록
ord-bbaaa807f5c24d0e9cdc9ab5afcdcf02
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353101B2

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