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

HRID 1297250노트

반응식

HRID 1297250 반응식
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

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 586751335-Biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-485c7f8e5807489ca7af22f1988bdef9
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250439B2

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