Hydrogen Peroxide → (R)-2-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutanoic acid

Participants

Reaction Steps

To a solution of (R)-4-benzyl-3-((R)-2-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutanoyl)oxazolidin-2-one (230 mg, 0.5 mmol) in 3:1 THF/H2O (8 mL) cooled in an ice-water bath, were added 30% aq H2O2 (0.5 mL, 3.5 mmol) and LiOH (60 mg, 1.1 mmol). The mixture was stirred at rt for 12 h. The mixture was cooled to 0° C. and 10% aq Na2SO3 (5 mL) was added dropwise. The solvent was removed in vacuo and the aqueous phase was washed with Et2O. The pH of the aqueous layer was adjusted to 3 by addition of 1 N aq HCl. The mixture was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, and evaporated to give (R)-2-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutanoic acid (123 mg, 81%). 1H NMR (400 MHz, CDCl3): 1.07 (m, 6H), 1.99 (m, 1H), 2.56 (m, 1H), 3.00 (m, 2H), 3.24 (m, 2H), 2.99 (s, 3H), 4.10 (m, 1H), 4.40 (m, 2H), 6.98 (m, 1H), 7.23 (m, 1H), 7.59 (m, 1H), 7.92 (m, 1H). MS: 305 (M++1)

Provenance & Evidence