Methanol → Methyl (2S)-2-amino-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate

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Reaction Steps

To a solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate (D83, 0.439, 1.0 mmol), prepared by an analogous procedure to that described hereinabove, in ethyl acetate (4.5 ml) and methanol (0.5 ml) at 0° C. was added dropwise AcCl (0.5 ml, 7.0 mmol) and the mixture was stirred from 0° C. to r.t. for four hours. The solvent was removed under vacuum. The residue was diluted with a saturated solution of sodium bicarbonate and extracted with dichloromethane. The organic layer was dried, filtered and evaporated affording the title compound as yellow oil (0.30 g, 91%). Rt (HPLC): 3.60 min; MS: (ES/+) m/z: 329 [MH]+ C18H17FN2O3 requires 328; 1H NMR (400 MHz, CDCl3) δ (ppm): 8.30-8.36 (m1H); 7.45-7.51 (m, 1H); 7.31-7.40 (m, 2H); 7.16-7.24 (m, 2H); 7.07-7.16 (m, 1H); 5.19 (s, 2H); 3.75-3.81 (m, 1H); 3.79 (s, 3H); 2.80-2.99 (m, 2H).

Provenance & Evidence