Trifluoroacetic acid → HCID 23081270, compound

HRID 856362Notes

Reaction equation

HRID 856362 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2([CH3:23])[O:16][C:15]3=[N:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][N:14]3[CH2:13]2)[C:7]1=[O:24].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:23][C:12]1([CH2:11][N:8]2[CH2:9][CH2:10][NH:6][C:7]2=[O:24])[O:16][C:15]2=[N:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][N:14]2[CH2:13]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 23081551HCID 23081551, compound

Product 1

HCID 23081270HCID 23081270, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2,4-dimethoxybenzyl)-3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)imidazolidin-2-one prepared in Example 594 (100 mg, 0.24 mmol), trifluoroacetic acid (2 ml) and methylene chloride (2 ml) was stirred at room temperature for 1 hour. To the reaction mixture, a saturated sodium hydrogencarbonate solution was added for neutralization. The resulting solution was extracted with methylene chloride. The organic phase was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was treated with diethyl ether to afford 1-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)imidazolidin-2-one (50 mg, yield 78%) as a white powder.

Workup

  1. extractionThe resulting solution was extracted with methylene chloride
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionthe residue was treated with diethyl ether

Sources & evidence

ORD record
ord-51a03617da174536b4020581d09b412c
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…