Sodium Hydroxide → t-Butyl (S)-2-(tert-butoxycarbonylamino)-6-hydroxyhexanoate

Participants

Reaction Conditions

Reaction Steps

A vigorously stirred solution of Boc-Lys-OtBu 2 (6.20 g, 20.5 mmol) in water (120 mL) and dioxane (60 mL) was warmed to 65° C. and treated with sodium nitroprusside (SNP, Na2[Fe(CN)5NO].2H2O) (9.8 g, 33 mmol) portionwise over 1 hour. The reaction mixture was stirred at 65° C. for an additional 4 hours while its pH was maintained at 9-10 by addition of 2M NaOH. It was then cooled to room temperature and filtered through a pad of CELITE. The filtrate was extracted with EtOAc (6×100 mL) and the combined extracts were dried (MgSO4), filtered, and evaporated in vacuo to give a purple oil. Its purification by flash chromatography (silica gel; hexanes/EtOAc, 8/1→3/7) gave the title compound 25 (2.28 g, 37%) as a clear oil.

Provenance & Evidence