Water → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-5'-(1-glycoloylpiperidin-4-yl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

HRID 607118노트

반응식

HRID 607118 반응식
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][C:24]=3[CH2:33][N:34]3[C@@H:38]([CH3:39])[C@@H:37]([C:40]4[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[C:42]([C:50]([F:53])([F:52])[F:51])[CH:41]=4)[O:36][C:35]3=[O:54])[C:17]([O:21][CH3:22])=[CH:18][C:19]=2[F:20])[CH2:10][CH2:9]1)=[O:7])(=O)C.C[O-].[Na+].O>CO>[F:53][C:50]([F:51])([F:52])[C:42]1[CH:41]=[C:40]([C@H:37]2[O:36][C:35](=[O:54])[N:34]([CH2:33][C:24]3[CH:25]=[C:26]([C:29]([F:31])([F:32])[F:30])[CH:27]=[CH:28][C:23]=3[C:16]3[CH:15]=[C:14]([CH:11]4[CH2:10][CH2:9][N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:13][CH2:12]4)[C:19]([F:20])=[CH:18][C:17]=3[O:21][CH3:22])[C@H:38]2[CH3:39])[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86630549HCID 86630549, 화합물

생성물 1

HCID 25009326(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-5'-(1-glycoloylpiperidin-4-yl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 2-{4-[2′-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-fluoro-6-methoxy-4′-(trifluoromethyl)biphenyl-3-yl]piperidin-1-yl}-2-oxoethyl acetate (24 mg, 0.031 mmol) in MeOH (1 mL) under N2 was added sodium methoxide (6.66 mg, 0.031 mmol). The resultant mixture was stirred at room temperature for 15 min. Water (10 mL) was added and the mixture was extracted with EtOAc (3×10 mL). The combined organic fractions were washed with brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-100% EtOAC/hexanes) to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4′-fluoro-5′-(1-glycoloylpiperidin-4-yl)-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one as a yellow gum. LCMS=737.1 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers) δ 7.87 (s, 1H), 7.69 (s, 2H), 7.68-7.60 (m, 2H), 7.34-7.30 (m, 1H), 6.96-6.91 (m, 1H), 6.72 (d, J=11.9 Hz, 1H), 5.44 (d, J=7.8 Hz, 1H), 4.90 (d, J=15.8 Hz, 1H), 4.78-4.70 (m, 1H), 4.18-4.13 (m, 2H), 3.78 (s, 3H), 3.62-3.54 (m, 1H), 3.15-3.05 (m, 2H), 2.82-2.73 (m, 1H), 1.96-1.84 (m, 2H), 1.70-1.52 (m, 4H), 0.43-0.39 (m, 3H).

후처리

  1. extractionthe mixture was extracted with EtOAc (3×10 mL)
  2. washThe combined organic fractions were washed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash silica gel chromatography (0-100% EtOAC/hexanes)

출처 및 근거

ORD 기록
ord-a47273755f5c423db29eec6ae104a383
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915271B2

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