(R)-tert-butyl 4-(2-(4-(4-methoxybenzyloxy)-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)-2,2,4-trimethyloxazolidine-3-carboxylate → (R)-tert-Butyl 4-(2-(4-hydroxy-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)-2,2,4-trimethyloxazolidine-3-carboxylate

HRID 2357082Notes

Reaction equation

HRID 2357082 reaction equation
COC1C=CC(C[O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:35])[CH2:16][NH:17][C:18]([C@@:20]3([CH3:34])[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[N:21]3[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:19])=[CH:11][C:10]=2[C:36]([F:39])([F:38])[F:37])=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:35])[CH2:16][NH:17][C:18]([C@@:20]2([CH3:34])[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[N:21]2[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])=[O:19])=[CH:11][C:10]=1[C:36]([F:38])([F:39])[F:37]

Participants

4

Reactant 1

HCID 59384449(R)-tert-butyl 4-(2-(4-(4-methoxybenzyloxy)-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)-2,2,4-trimethyloxazolidine-3-carboxylate

Product 1

HCID 59384415(R)-tert-Butyl 4-(2-(4-hydroxy-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)-2,2,4-trimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 4-(2-(4-(4-methoxybenzyloxy)-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)-2,2,4-trimethyloxazolidine-3-carboxylate (4) (2.4 g, 4.1 mmol, 1.0 equiv) in methanol (20 mL) was added 10% Pd/C (240 mg). The reaction mixture was stirred for 3 hours at rt under H2 atmosphere using a H2 balloon, filtered through celite and concentrated to give (R)-tert-butyl 4-(2-(4-hydroxy-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)-2,2,4-trimethyloxazolidine-3-carboxylate (6a) as a white foam in quantitative yield. HPLC retention time on a C18 column (30×4.6 mm, 3.5μ) was 2.62 min with gradient 10-95% acetonitrile-H2O (0.1% TFA) in 3.5 min as mobile phase. MS (ESI, M+H+)=461.4.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-29ab6a71a2794ff1aa48e4ce6f34ef0e
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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