Succinic anhydride → 3-(N-(2-methyl-2-sulfanylpropyl)carbamoyl)propanoic acid

Temperature

0 °C

To an ice-cooled suspension of 1-amino-2-methylpropan2-thiol hydrochloride (5.06 g, 35.72 mmol) in methylene chloride (100 mL) was added triethylamine (5.0 mL, 35.87 mmol) followed by succinic anhydride (3.50 g, 34.96 mmol). The resulting clear solution was stirred at 0° C. or 10 minutes, then at room temperature for 2 hours. Evaporation of the volatiles under reduced pressure gave a residue which was partitioned between 2 N hydrochloric acid (100 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine (5 mL), dried over sodium sulfate and evaporated to dryness. The residue was triturated with ether-hexane to afford the title compound as a white solid (6.78 g, 94.4%). Mp. 86-87° C.; 1H NMR (300 MHz, CDCl3): δ1.34 (s, 6H), 1.55(s, 1H), 2.59 (t, J=6.6 Hz, H), 2.70 (t, J=6.6 Hz, 2H), 3.32 (d, J=8.0 Hz, 2), 6.58 (br t, J=5.9 Hz, 1H), 10.73 (br s, 1H); 13C NMR (75 MHz, CDCl3): δ29.57, 29.79, 30.79, 172.50, 176.81; LCMS (m/e): 223 (M+H2O), 206 (M+1).

1. waitat room temperature for 2 hours
2. customEvaporation of the volatiles under reduced pressure
3. customgave a residue which
4. customwas partitioned between 2 N hydrochloric acid (100 mL) and ethyl acetate (100 mL)
5. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
6. washThe combined organic layers were washed with brine (5 mL)
7. dry with materialdried over sodium sulfate
8. customevaporated to dryness
9. customThe residue was triturated with ether-hexane

ORD record

ord-5c8fcc42009f4451b3b20f6558b28db8

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06552047B2