Water → HCID 24780800, compound

Participants

Reaction Steps

tert-Butyl (2-fluoroethyl)[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]carbamate (0.65 mmol) was dissolved in CH2Cl2 (20 mL), trifluoroacetic acid (0.5 mL) was added and the reaction mixture was stirred for 4 hours at r.t. Water (20 mL), NaOH (1.5 mL, 5M aq., pH adjusted to 12) and CH2Cl2 (20 mL) was added and the layers separated. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried (Na2SO4) filtered and concentrated. Purification using reverse phase HPLC afforded the title compound (78.0 mg). 1H NMR δ ppm 8.74 (d, 1H) 8.03 (dd, 1H) 7.60-7.64 (m, 1H) 7.58 (d, 1H) 7.35 (d, 1H) 6.95 (dd, 1H) 6.70 (d, 1H) 4.60-4.66 (m, 1H) 4.47-4.54 (m, 1H) 3.82 (s, 3H) 3.67-3.74 (m, 1H) 3.60-3.67 (m, 1H); ESI-MS m/z 288 (M+H).

Provenance & Evidence