Dimethylformamide → HCID 86715339, compound

Temperature

0 °C

To a solution of (1R,3S)-3-(methoxycarbonyl)cyclopentanecarboxylic acid (130 mg, 0.76 mmol) in dichloromethane (3 mL) was added DMF (5.85 μL, 0.08 mmol). The solution was cooled to 0° C. oxalyl chloride (73.0 μL, 0.83 mmol) was added. The mixture was stirred at 0° C. for 30 minutes and then allowed to warm to room temperature for one hour. The reaction was re-cooled to 0° C., 2-(trimethylsilyl)thiazole (178.0 mL, 1.13 mmol) was added and the mixture was stirred at room temperature for two hours. The mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford (1S,3R)-methyl 3-(thiazole-2-carbonyl)cyclopentanecarboxylate. MS ESI calc'd. for C11H14NO3S [M+H]+ 240. found 240. 1H NMR (500 MHz, DMSO-d6) δ 8.21 (d, J=3.0 Hz, 1H), 8.14 (d, J=3.0 Hz, 1H), 3.58 (s, 3H), 2.96-2.89 (m, 1H), 2.27-2.20 (m, 1H), 1.74-2.04 (m, 6H)

1. additionwas added
2. temperatureto warm to room temperature for one hour
3. temperatureThe reaction was re-cooled to 0° C.
4. stirringthe mixture was stirred at room temperature for two hours
5. washwashed with saturated sodium bicarbonate
6. customThe organic layer was separated
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by column chromatography on silica gel

ORD record

ord-0c34b910327048d0adb8ec33b57909d1

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120785B2