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, 29.7 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).

1. concentrationwas concentrated under vacuum
2. additionCold 2N HCl (50 mL) was added to the residue
3. extractionThe mixture was extracted with EtOAc (5×30 mL)
4. washThe combined organic extracts were washed with brine (30 mL)
5. dry with materialdried over Na2SO4
6. concentrationConcentration and trituration with Et2O

ORD record

ord-cacda67cb1474b0a9bcf0fdb05b3da7f

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06593347B2