Sodium Hydroxide → HCID 178461692, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate 14b (1.09 g, 2.80 mmol) was dissolved in a solution of NaOH (0.11 g, 2.75 mmol) in CH3OH (10 ml). The reaction mixture was stirred for 1 h at 50° C. and then quenched with a saturated solution of NH4Cl (10 ml); the aqueous layer was extracted with CH2Cl2 (2×10 ml) and the combined organic phases, after drying over anhydrous Na2SO4, were evaporated under vacuum and crystallized from n-heptane to give the pure 4-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)ethyl]-1,2,5-thiadiazol-3-ol (14) (0.625 g, 1.68 mmol) as a white solid (60%). [α]D=−33 (c=1; CH3OH); 1H-NMR (CDCl3): δ 9.25 (bs, 1H, NH), 8.35 (bs, 1H, OH), 7.40 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 7.00 (s, 1H), 3.85 (q, 1H, J=7 Hz) 1.75 (d, 3H, J=7 Hz).

Provenance & Evidence