Triethylamine → HCID 18710120, compound

Participants

Reaction Steps

In a procedure similar to the preparation of sulfamide (8b), H-Ala-OMe.HCl (2.18 g, 15.56 mmol) was subjected to sulfamide formation conditions (SO2Cl2, Et3N, CH2Cl2 0° C., room temperature, 2 hours). Flash chromatography (SiO2, Hexanes/EtOAc) yielded 617 mg (31%) of sulfamide (8a) as a white solid. mp=91-92° C.; TLC Rf=0.40 in (2:1 Hexanes/EtOAc); [α]25D=−75.8 (c=1.003, CHCl3); 1H NMR (CDCl3, 400 MHZ) δ5.24 (d, J=8.0 Hz, 2H), 4.09 (dq, J=7.3.7.3 Hz, 2H), 3.75 (s, 6H), 1.43 (d, J=7.2 Hz, 6H); 13C NMR (CDCl3, 100 MHZ) δ173.7,52.7,51.8,19.2; FTIR (neat) 3273, 1734, 1457, 1378, 1353, 1137 cm−1; HRMS (M+H)+ calculated for C8H17N2O6S 269.0807, found 269.0791.

Provenance & Evidence