Hexamethyldisilazane → HCID 18626619, compound

Temperature

0 °C

A mixture of 2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid (450 mg, 1.51 mmol) in methylene chloride (4 mL) was treated with N,N-dimethylformamide (1 drop) and then cooled to 0° C. The reaction mixture was then slowly treated with oxalyl chloride (145 μL, 1.66 mmol). The reaction mixture was stirred at 0° C. for 10 min and then stirred at 25° C. for 1 h. The resulting reaction mixture was then treated dropwise with 1,1,1,3,3,3-hexamethyldisilazane (960 μL, 4.53 mmol) and subsequently stirred at 25° C. for 15 h. The resulting reaction mixture was diluted with methylene chloride (10 L) and methanol (10 mL). The organic layer was washed with a 5% aqueous sulfuric acid solution and a saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionamide (295 mg, 67%) as a yellow oil which solidified upon sitting to a yellow solid. The yellow solid was used without further purification: mp 112-114° C.; EI-HRMS m/e calcd for C14H17ClN2O3 (M+) 296.0927, found 296.0931.

1. stirringstirred at 25° C. for 1 h
2. customThe resulting reaction mixture
3. stirringsubsequently stirred at 25° C. for 15 h
4. customThe resulting reaction mixture
5. washThe organic layer was washed with a 5% aqueous sulfuric acid solution
6. dry with materialThe organic layer was dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-366b991bc0a74564a1d2f6aa2af9a685

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06528543B1