Sodium Bisulfate → tert-Butyl {(1S)-1-methyl-2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 985165ノート

反応式

HRID 985165 の反応式
CON(C)[C:4](=[O:11])[C@@H:5]([NH:7][C:8](=[O:10])[O-:9])[CH3:6].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.S([O-])(O)(=O)=O.[Na+]>O1CCCC1>[F:13][C:14]([F:24])([F:23])[C:15]1[CH:20]=[CH:19][C:18]([C:4](=[O:11])[C@@H:5]([NH:7][C:8](=[O:10])[O:9][C:15]([CH3:20])([CH3:16])[CH3:14])[CH3:6])=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 516919Sodium BisulfateHCID 86589062N-{(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamateHCID 178506198HCID 178506198、化合物

生成物 1

HCID 59339706tert-Butyl {(1S)-1-methyl-2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl}carbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of N-{(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamate (9.6 g) in tetrahydrofuran (180 mL) was dropwise added at 0° C. to a solution of 1.48M 4-trifluoromethylphenylmagnesium bromide in tetrahydrofuran (70 mL) which had been prepared in another batch. The mixture was stirred at room temperature for 14 hours, and cooled down to 0° C. After addition of aqueous sodium hydrogen sulfate, the reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and filtered to remove the sodium sulfate. Evaporation of the organic solvent in vacuo gave t-butyl N-[(1S)-2-(4-trifluoromethylphenyl)-1-methyl-2-oxoethyl]carbamate (13.4 g) as an orange solid.

後処理

  1. customhad been prepared in another batch
  2. temperaturecooled down to 0° C
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customto remove the sodium sulfate
  8. customEvaporation of the organic solvent in vacuo

出典と根拠

ORDレコード
ord-d5d38341b1d5426eb138d104d6a8e0cd
出典データセット
uspto-grants-2005_03
特許番号
US06869966B2

反応ノート

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