Sodium Thiosulfate → HCID 86694363, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-benzyl (1-hydroxypropan-2-yl)(4-methoxybenzyl)carbamate (11.8 g, 35.5 mmol) in CH2Cl2 was added NaHCO3 (3.28 g, 39 mmol), KBr (0.25 g, 2.1 mmol) and TEMPO 0.168 g, 1.07 mmol). The reaction mixture was cooled to 0-5° C. and the 5% aqueous NaClO solution (85 mL, 71 mmol) was added within 30 min. After stirring for 1 h at 0-5° C. the reaction mixture was added to Na2S2O3 solution and the product was extracted with EtOAc. Combined extracts were washed with aqueous NaH2PO4 solution, H2O and brine, dried over MgSO4, filtered and concentrated to provide the title compound as a yellow oil (11.2 g, 96%): TLC (hexane/EtOAc 1:1) Rf=0.55; tR=1.29 min (UPLC 1), tR, 1.15 min (LC-MS 3); ESI-MS: 328 [M+H]+ (LC-MS 3).

Provenance & Evidence