Triethylamine → 2-Oxo-oxazolidine-3-sulfonic acid (2-phenyl-cyclopropyl)-amide

Temperature

0 °C

To a round bottom flask was added chlorosulfonyl isocyanate (0.4 mL, 4.64 mmol) and methylene chloride (5 mL) under an atmosphere of argon. The mixture was cooled in an ice bath and 2-bromoethanol (0.535 mL, 7.55 mmol) in methylene chloride (1 mL) was added dropwise. After stirring for 30 minutes at 0° C., triethylamine (2.28 mL, 16.4 mmol) and trans-2-phenylcyclopropylamine hydrochloride (0.867 g, 5.11 mmol), 6a, in methylene chloride (5 mL) was added at such a rate that the reaction temperature was maintained between 0° C. and 10° C. The resulting solution was stirred at rt for 5 h and then partitioned between 1N HCl and water. The organic layer was dried with sodium sulfate, filtered and concentrated. The crude was purified by chromatography to give 569 mg of a waxy solid, 8a. 1H NMR (300 MHz, DMSO-d6): δ 7.34-7.22 (m, 3H), 7.12 (d, J=7.0 Hz, 2H), 6.00 (s, 1H), 4.50-4.33 (m, 2H), 4.16-3.95 (m, 2H), 2.66-2.61 (m, 1H), 2.43-2.37 (m, 1H), 1.48-1.41 (m, 1H), 1.30 (q, J=6.5 Hz, 1H). MS m/z: 283 (M+1).

1. temperatureThe mixture was cooled in an ice bath
2. temperaturewas maintained between 0° C. and 10° C
3. stirringThe resulting solution was stirred at rt for 5 h
4. custompartitioned between 1N HCl and water
5. dry with materialThe organic layer was dried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude was purified by chromatography

ORD record

ord-d8bfaea824454857b9527db3af640bfd

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338608B2