Ethyl Acetate → HCID 19698551, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing 100 mg (0.239 mmol) of 3-[4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]oxazol-2-yl]propanoic acid, methyl ester in 10 mL of tetrahydrofuran was cooled to 0° C. with stirring under a nitrogen atmosphere as 0.53 mL of diisobutylaluminum hydride (1M in toluene, 0.523 mmol) was added dropwise over 5 minutes. The reaction was allowed to warm to 25° C. and poured into 100 mL of a saturated solution of sodium potassium tartarate. Ethyl acetate (100 mL) was added and the mixture was stirred until the layers separated (approx. 1 hour). The organic layer was separated and dried over sodium sulfate. Concentration in vacuo gave an oily solid, which was recrystallized from 50% ethyl acetate-isooctane to give 75 mg of a white crystalline solid (mp 123°-124° C.) which was characterized on the basis of its spectral characteristics: 1H-NMR (CDCl3, 300 MHz) ∂ 2.10 (m, 2H), 2.56 (bs, 1H), 3.01 (t, 2H, J=7.0 Hz), 3.07 (s, 3H), 3.80 (t, 2H, J=5.9 Hz), 7.09 (t, 2H, J=8.5 Hz), 7.57 (dd, 2H, J=8.5 and 5.5 Hz), 7.73 (d, 2H, J=8.5 Hz) and 7.89 (d, 2H, J=8.5 Hz). 19F-NMR (CDCl3, 280 MHz) ∂-111.97. LRMS m/z 376 (M+H)+. HRMS calc. for C19H18NO4FS: 376.1019. Observed: 376.1026. Analysis calc. for C19H18NO4FS-C: 60.79, H: 4.83, N: 3.73. Observed-C: 60.53, H: 4.85, N: 3.66.

Provenance & Evidence