Water → HCID 22993473、化合物

HRID 1167729ノート

反応式

HRID 1167729 の反応式
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

参加物

5

反応物 3

HCID 962WaterHCID 24758Sodium hydrideHCID 22993581HCID 22993581、化合物

生成物 1

HCID 22993473HCID 22993473、化合物収率 100.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f2180771c18d423b8110914d2ef07c25
出典データセット
uspto-grants-2003_09
特許番号
US06620815B1

反応ノート

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