Triethylamine → 2-{[N-(2-methyl-2-sulfanylpropyl)carbamoyl]methoxy}acetic acid

Participants

Reaction Steps

To an ice-cooled suspension of 1-amino-2-methyl-2-propanethiol hydrochloride (4.21 g, 29.7 mmol) in CH2Cl2 (50 mL) was added Et3N (4.56 mL, 32.7 mmol) followed by diglycolic anhydride (3.43 g, 29.6 mmol). After stirring at room temperature for 30 minutes the reaction was concentrated under vacuum. Cold 2N HCl (50 mL) was added to the residue. The mixture was extracted with EtOAc (5×30 mL). The combined organic extracts were washed with brine (30 mL) and dried over Na2SO4. Concentration and trituration with Et2O:hexane gave the title compound as a white solid (5.50 g, 84.2%). mp 81-82° C.; 1H NMR (300 MHz, CDCl3) δ 8.80 (br s, 1H), 7.48 (br s, 1H), 4.24 (s, 2H), 4.20 (s, 2H), 3.41 (d, J=6.4 Hz, 2H), 1.59 (s, 1H), 1.38 ((s, 6H); 13C NMR (75 MHz, CDCl3) δ 172.8, 170.4, 70.8, 68.4, 51.9, 44.9, 29.8; mass spectrum (API-TIS) m/z 239 (M+NH4), 222 (M+H).

Provenance & Evidence