Hydrochloric Acid → HCID 54444285, compound

Participants

Reaction Steps

The acetylated thiol 7 (290 mg, 0.82 mmol) was dissolved in methanol (4 mL) and NaOH was added (4.1 mL, 0.2N aqueous). The reaction was stirred at room temperature for 20 min (monitored by TLC). The solution was then carefully neutralized with dilute HCl. The volatiles were removed in vacuo and the residue was extracted with Cl2CH2 (3×). The organic layer was washed with brine and dried over Na2SO4. The crude product was purified by flash column chromatography (silica, 10% ethyl acetate/hexane) to give the desired thiol 9 (242 mg, 95%) as a white solid. mp 76°-77° C. (ether-hexane); [α]20D =+92.3 (c=0.96, CHCl3); 1H NMR (CDCl3).δ1.392 (s, 9H), 2.207 (d, J=7.3 Hz, SH), 3.698 (s, 3H), 4.471 (dd, J=6.7, 6.3 Hz, 1H, CH--S), 4.800 (dd, J=8.7, 6.3 Hz, 1H, CH--N), 5.059 (bd, J=8.7 Hz, 1H, NH), 7.370-7.282 (m, 5H); 13C NMR (CDCl3).δ28.0, 52.1, 59.5, 80.1, 127.5, 127.6, 128.8, 138.8, 155.9, 171.5; IR (KBr) 3335, 2990, 1740, 1685, 1530, 1165 cm-1 ; MS m/z 312 [M+H]+ ;. Anal. Calcd. for C15H21O4NS: C, 57.88; H, 6.75. Found: C, 58.08; H, 6.88.

Provenance & Evidence