Potassium Hydroxide → 3-(2-Hydroxy-5-(Ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoic acid

Participants

Reaction Steps

A solution of 120 (0.99 g, 2.4 mmol) and KOH (0.095 g, 2.4 mmol) in methanol was stirred at room temperature for 2 hr. The solvent was removed removed under reduced pressure and the product was resuspended in water, the pH was adjusted to 4 by the addition of HCl, and the product was extracted with CH2Cl2. The organics were dried over Na2SO4, filtered and concentrated, resulting in 121 as a pale yellow oil (1.1 g, 105%) which was used without purification. 1H NMR (400 MHz, CDCl3) δ 1.26 (t, J=7.2, 3H), 1.29-1.37 (m, 6H), 1.45 (s, 3H), 1.48 (s, 3H), 2.63 (dd, J=17.7, 20.9, 2H), 2.93 (AB q, J=14.2, 2H), 4.00-4.20 (m, 6H), 6.74 (bs, 1H), 7.56 (ddd, J=1.6, 8.5, 12.2, 2H), 7.63 (d, J=13.3, 1H).

Provenance & Evidence