Ethyl Acetate → (4S,5R)-5-(3,5-Bis-trifluoromethyl-phenyl)-3-(2-bromo-5-trifluoromethyl-benzyl)-4-methyl-oxazolidin-2-one

HRID 456219

반응식

HRID 456219 반응식
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[NH:15][C@H:14]2[CH3:19])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C[Si](C)(C)N[Si](C)(C)C.[Na].[Br:32][C:33]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:34]=1[CH2:35]Br.CCOC(C)=O>C1COCC1.O>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:35][C:34]3[CH:37]=[C:38]([C:41]([F:42])([F:44])[F:43])[CH:39]=[CH:40][C:33]=3[Br:32])[C@H:14]2[CH3:19])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 27562491-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzeneHCID 23583229(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-oneHCID 45051731Sodium hexamethyidisilazane

생성물 1

HCID 86650342(4S,5R)-5-(3,5-Bis-trifluoromethyl-phenyl)-3-(2-bromo-5-trifluoromethyl-benzyl)-4-methyl-oxazolidin-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To (4S,5R)-5-(3,5-bis-trifluoromethyl-phenyl)-4-methyl-oxazolidin-2-one (0.246 g, 0.79 mmol) in THF (10 mL) at mom temperature was added sodium hexamethyldisilazane (1M in THF; 1.02 mL, 1.02 mmol), and the reaction was stirred for 15 minutes. 2-Bromo-5-(trifluoromethyl)benzyl bromide (0.250 g, 0.79 mmol) was added, and the reaction was stirred overnight at room temperature. The mixture was worked-up with EtOAc and H2O, and the crude material was purified by silica gel chromatography to give the title compound.

후처리

  1. stirringthe reaction was stirred overnight at room temperature
  2. customthe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-8cbfbc09ef2b4a38957e0139f357c329
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497381B2

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