Lithium Hydroxide → HCID 67252591, compound

Participants

Reaction Conditions

Reaction Steps

A solution of {6-[2-(2-tert-butoxycarbonylamino-ethylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid ethyl ester (0.35 g, 0.72 mmol) in THF (5 mL) was treated with lithium hydroxide (0.084 g, 3.60 mmol) in water (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour then at room temperature for 1 hour. The mixture was quenched with 2N HCl to pH 2 then concentrated to approximately half of the entire volume. The mixture was diluted with brine and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), filtered and concentrated to give {6-[2-(2-tert-butoxycarbonylamino-ethylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid, as a light yellow solid (0.18 g) after lyophilization. The aqueous layer was lyophilized, diluted with water (3 mL) and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), filtered and concentrated to a light yellow solid after lyophilization, to give a total of 0.21 g (64%) of product. 1H NMR (400 MHz, CD3OD) δ8.13 (d, J=6.64 Hz, 1H), 7.25 (s, 1H), 7.12 (s, 1H), 6.46 (m, 1H), 5.67 (dd, J=8.21, 2.40 Hz, 1H), 3.17 (dd, J=15.63, 3.13 Hz, 1H), 3.20-3.00 (m, 3H), 2.38 (br s, 4H), 1.40 (br s, 10H).

Provenance & Evidence