Trifluoroacetic acid → 5-Biphenyl-4-yl-3-hydroxy-2-methyl-pentanoic acid

HRID 1297250ノート

反応式

HRID 1297250 の反応式
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:32])[CH:14]([CH3:31])[C:15](=[O:30])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)(C)(C)C>ClCCl>[C:21]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][CH:15]([OH:30])[CH:14]([CH3:31])[C:13]([OH:32])=[O:12])=[CH:23][CH:22]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 586751335-Biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester2 回

生成物 1

HCID 112083685-Biphenyl-4-yl-3-hydroxy-2-methyl-pentanoic acid収率 56%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of trifluoroacetic acid in dichloromethane (20%; 10 mL) was added to 5-biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester (Intermediate 7, 130 mg, 0.382 mmol) and the resulting solution stirred at room temperature for 1.5 hour. The volatiles were evaporated under reduced pressure and the residue was purified by column chromatography on silica gel (1:2 ethyl acetate: 40–60 petroleum ether) to give the title compound (60 mg, 56%) as a white solid, mixture of diastereoisomers. LC/MS: 3.22 min; z/e 302, calcd (M+NH4) 302. 1H NMR (400 MHz: CDCl3): 7.59 (2 H), 7.51 (2 H), 7.40 (2 H), 7.28 (3 H), 4.21, 4.01 3.75, 2.91, 2.76, 2.62, 1.88, 1.25.

後処理

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (1:2 ethyl acetate: 40–60 petroleum ether)
  3. customto give

出典と根拠

ORDレコード
ord-485c7f8e5807489ca7af22f1988bdef9
出典データセット
uspto-grants-2007_07
特許番号
US07250439B2

反応ノート

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