Potassium Hydroxide → HCID 69133356, compound

Participants

Reaction Steps

A solution of 3β-aminoandrostane-6,17-dione hydrochloride (150 mg) in CH2Cl2 was treated with powdered KOH (25 mg) and stirred for 15 min. 4-(tert-Butoxycarbonylamino)butyric acid (98 mg), EDAC (168 mg) and 4-dimethylaminopyridine (8 mg) were added at 0° C. The reaction temperature was raised to room temperature and stirred for 24 hrs. The mixture was washed with water (2×10 mL) and 5% NaHCO3 (10 mL). The organic layer was dried and evaporated to dryness. The residue was purified by flash chromatography (SiO2; CH2Cl2:MeOH:NH3 9:1:0.1) to give 3β-[4-(tert-butoxycarbonylamino)butyramido]-androstane-6,17-dione (161 mg, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.68 (1H, d), 6.77 (1H, t), 3.46 (1H, m), 2.87 (2H, m), 2.45-1.10 (24H, m), 1.36 (9H, s), 0.78 (3H, s), 0.66 (3H, s).

Provenance & Evidence