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

HRID 456217

反応式

HRID 456217 の反応式
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

参加物

8

反応物 4

HCID 6422Trifluoroacetic acidHCID 13014DimethylphenylsilaneHCID 14797Potassium HydroxideHCID 11589807HCID 11589807、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e2a23c883e554802a7ea3f3a7bbf9332
出典データセット
uspto-grants-2013_07
特許番号
US08497381B2

関連ノート

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