Water → HCID 22993473, 화합물

HRID 1167729노트

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HRID 1167729 반응식
C([O:5][C:6](=[O:22])[NH:7][CH:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)[CH:9]([CH:11]1[CH2:13][CH2:12]1)O)(C)(C)C.[H-].[Na+].O>C1COCC1>[CH:11]1([CH:9]2[O:22][C:6](=[O:5])[NH:7][CH:8]2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[CH2:12][CH2:13]1

참가 물질

5

반응물 3

HCID 962WaterHCID 24758Sodium hydrideHCID 22993581HCID 22993581, 화합물

생성물 1

HCID 22993473HCID 22993473, 화합물수율 100.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
35 °C

실험 절차

To a well stirred solution of [2-cyclopropyl-1-(3,4-difluorophenyl)-2-hydroxy-ethyl]-carbamic acid-tert-butyl ester (1.7 g, 5.4 mmol) in THF (20 mL) was added 95% NaH (0.4 g, 16.2 mmol) at room temperature. The resulting suspension was stirred for 3 h at about 35° C. (warm water bath) and then quenched carefully with ice. The biphasic mixture was extracted with 100 mL of EtOAc, washed with brine, dried over Na2SO4, filtered and the solvent was removed in vacuo to yield 5-cyclopropyl-4-(3,4-difluorophenyl)-oxazolidin-2-one (1.3 g, 93% yield) as a 3:1 mixture of the trans:cis diastereomers. The diastereomers were separated by column chromatography over silica gel with 7:3 cyclohexane/ethylacetate as the eluting system. The trans isomer eluted first (Rf=2.5, 0.65 g) followed by the cis isomer (Rf=2.0, 0.2 g). The relative streochemistry was assigned by comparing the 1H NMR of the two isomers of 5-cyclopropyl-4-(3,4-difluorophenyl)-oxazolidin-2-one to the corresponding isomers of 4-(3,4-difluorophenyl)-5-methyl-oxazolidin-2-one as described in Example 19.

후처리

  1. customquenched carefully with ice
  2. extractionThe biphasic mixture was extracted with 100 mL of EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-f2180771c18d423b8110914d2ef07c25
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620815B1

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