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

To an ice-cooled suspension of 1-amino-2-methylpropane-2-thiol 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). After stirring at room temperature for 30 minutes, the reaction was concentrated in vacuo and cold 2 N HCl (50 mL) was added to the residue. The mixture was extracted with ethyl acetate (5×30 mL). The combined extracts were washed with brine (30 mL) and dried over anhydrous sodium sulfate. Volatiles were evaporated and the residue was triturated with ether/hexane to afford 5.50 g (84%) of the title compound as a white solid. mp 81-82° C.; 1H NMR (CDCl3, 300 MHz): δ1.38 (s, 6H), 1.59 (s, 1H), 3.41 (d, 2H, J=6.4 Hz), 4.20 (s, 2H), 4.24 (s, 2H), 7.48 (br s, 1H), 8.80 (br s, 1H); 13C NMR (CDCl3, 75 MHz) δ29.83, 44.91, 51.90, 68.39, 70.77, 170.40, 172.84; LCMS (m/e): 239 (M+H2O), 222 (M+1).

1. concentrationthe reaction was concentrated in vacuo and cold 2 N HCl (50 mL)
2. additionwas added to the residue
3. extractionThe mixture was extracted with ethyl acetate (5×30 mL)
4. washThe combined extracts were washed with brine (30 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. customVolatiles were evaporated
7. customthe residue was triturated with ether/hexane

ORD record

ord-59be6c0daf314b05b0935bd047cd6f65

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06469065B1