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, 29.72 mmol) in methylene chloride (50 mL) was added triethylamine (4.56 mL, 32.72 mmol) followed by diglycolic anhydride (3.43 g, 29.55 mmol). The solution was stirred at room temperature for 30 min and the reaction concentrated under vacuum. Cold 2N HCl (50 mL) was added to the residue and the mixture was extracted with ethyl acetate. The combined extracts were washed with brine and dried (sodium sulfate). Evaporation and trituration with ether/hexane gave the title compound as a white solid (5.50 g, 84%). 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, 70.7, 68.3, 51.9, 44.9, 29.8. LRMS (APIMS) m/z 222 (MH+), 239 (M+NH4+).

Provenance & Evidence