m-Chloroperbenzoic acid → benzyl (2R)-2-benzyl-5-tert-butylsulfinyl-4-oxopentanoate

Participants

Reaction Steps

The resultant compound from Example 37 (44.4 mg, 0.115 mmol) in CH2Cl2 (2 ml) at -10° C. was treated with meta-chloroperbenzoic acid (25.0 mg, 0.116 mmol, 80% pure). After 2 h at -10°-0° C. the solvent was evaporated and the residue was dissolved in ethyl acetate which was washed with 1:1 10% Na2SO4 solution/ saturated NaHCO3 solution, saturated NaHCO3 solution and brine, and then dried over Na2SO4 and evaporated to afford 46.0 mg (99%) of a colorless oil. 1H NMR (CDCl3) δ7.05-7.40 (m,10H), 5.08 (m,2H), 3.36-3.53 (m,2H), 3.30 (m,1H), 2.95-3.18 (m,2H), 2.80 (2dd,total 1H), 2.69 (2dd,total 1H), 1.24 (s,9H).

Provenance & Evidence