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

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) δ8.80 (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) δ172.8, 170.4, 70.7, 68.3, 5.19, 44.9, 29.8. LRMS (APIMS) m/z 222 (MH+), 239 (M+NH4+).

1. concentrationthe reaction concentrated under vacuum
2. additionCold 2N HCl (50 mL) was added to the residue
3. extractionthe mixture was extracted with ethyl acetate
4. washThe combined extracts were washed with brine
5. dry with materialdried (sodium sulfate)
6. customEvaporation and trituration with ether/hexane

ORD record

ord-be55479ea08440bb8cdcba0546477e46

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06656966B2