Trifluoroacetic acid → [(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl ester

HRID 456217

반응식

HRID 456217 반응식
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16](=[O:36])[NH:17][C@@H:18]([CH3:35])[C:19]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[SiH](C)C1C=CC=CC=1.[OH-].[K+]>CCOC(C)=O.[Cl-].[Na+].O.C1COCC1>[CH2:8]([O:15][C:16](=[O:36])[NH:17][C@@H:18]([CH3:35])[CH:19]([C:21]1[CH:22]=[C:23]([C:31]([F:32])([F:33])[F:34])[CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)[OH:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

8

반응물 4

HCID 6422Trifluoroacetic acidHCID 13014DimethylphenylsilaneHCID 14797Potassium HydroxideHCID 11589807HCID 11589807, 화합물

생성물 1

HCID 58604019[(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl ester

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

Trifluoroacetic acid (11 mL) was cooled to −5° C. [(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-1-methyl-2-oxo-ethyl]-carbamic acid benzyl ester (5 g, 11.9 mmol) was added slowly, followed by dimethylphenylsilane (2.2 mL, 14.3 mmol), and the mixture was stirred for 4 hours. Once no starting material was seen by analytical tlc, the mixture was cooled to 0° C. and treated with 50% aqueous KOH (12 mL), followed by THF (16 mL). After stirring at room temperature for 5 hours, only starting material was seen by analytical tlc, and so the solution was diluted with EtOAc and brine. The organic layer was separated and concentrated, and the crude material was purified by silica gel chromatography to give the title compound.

후처리

  1. additionwas added slowly
  2. stirringAfter stirring at room temperature for 5 hours
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customthe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-e2a23c883e554802a7ea3f3a7bbf9332
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497381B2

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