2-Pyrrolidone → HCID 57461786, compound

HRID 1020340Notes

Reaction equation

HRID 1020340 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.Br[C:10]1[O:11][C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1>CN(C=O)C>[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[O:11][C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]([C:15]([F:17])([F:16])[F:18])[N:14]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 53403202Ethyl 2-bromo-4-(trifluoromethyl)-1,3-oxazole-5-carboxylate

Product 1

HCID 57461786HCID 57461786, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

NaH (0.060 mg, 1.5 mmol) (60%) was added to a solution of 2-oxopyrrolidine (0.13 g, 1.5 mmol) in DMF (5.0 mL) at −78° C. followed by stirring for 15 mins at −78° C. Then ethyl 2-bromo-4-trifluoromethyloxazole-5-carboxylate A-2 (0.29 g, 1.0 mmol) was added. The reaction mixture was stirred for 3 h while the temperature was slowly warmed to RT. The reaction mixture was purified by chromatography on a Prep Gilson HPLC to yield ethyl 2-(2-oxopyrrolidin-1-yl)-4-(trifluoromethyl)oxazole-5-carboxylate (A-30) as a white solid (0.15 g, 34% yield). 1H NMR (500 MHz, CDCl3) δ 4.44 (m, 2H), 4.09 (t, 2H, J=7.0 Hz), 2.69 (t, 2H, J=8.2 Hz), 2.28 (m, 2H), 2.42 (t, 3H, J=7.3 Hz).

Workup

  1. stirringThe reaction mixture was stirred for 3 h while the temperature
  2. temperaturewas slowly warmed to RT
  3. customThe reaction mixture was purified by chromatography on a Prep Gilson HPLC

Sources & evidence

ORD record
ord-3b5624521ff742b9b6d750afeec36938
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

Loading…