Trifluoroacetic acid → 4-(Benzyloxy)-3-(biphenyl-4-ylmethyl)-4-oxobutanoic acid

HRID 333320Notes

Reaction equation

HRID 333320 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:12]([O:11][C:9](=[O:10])[CH:8]([CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:6][CH:5]=1)[CH2:19][C:20]([OH:22])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687488041-Benzyl 4-tert-butyl 2-(biphenyl-4-ylmethyl)succinate

Product 1

HCID 687501454-(Benzyloxy)-3-(biphenyl-4-ylmethyl)-4-oxobutanoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl 4-tert-butyl 2-(biphenyl-4-ylmethyl)succinate (90 mg, 0.209 mmol) in DCM (1 ml), TFA (0.322 ml, 4.18 mmol) was added. The reaction mixture was allowed to stir for 1 hour, and then concentrated under reduced pressure to give 4-(benzyloxy)-3-(biphenyl-4-ylmethyl)-4-oxobutanoic acid (78 mg); Retention time=1.48 minutes (condition B); MS (m−1)=373.2.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2410e09f4d6b4dd6ae711211307a44a1
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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