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

HRID 1297250Notes

Reaction equation

HRID 1297250 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-485c7f8e5807489ca7af22f1988bdef9
Source dataset
uspto-grants-2007_07
Patent number
US07250439B2

Reaction notes

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