Sodium Hydroxide → HCID 20680715, compound

HRID 651622Notes

Reaction equation

HRID 651622 reaction equation
C([NH:4][C:5]1[CH:24]=[CH:23][C:8]([CH2:9][N:10]2[CH2:14][CH2:13][C@H:12]([NH:15]C(=O)C(F)(F)F)[C:11]2=[O:22])=[CH:7][C:6]=1[N+:25]([O-:27])=[O:26])(=O)C.[OH-].[Na+]>CCO>[NH2:15][C@H:12]1[CH2:13][CH2:14][N:10]([CH2:9][C:8]2[CH:23]=[CH:24][C:5]([NH2:4])=[C:6]([N+:25]([O-:27])=[O:26])[CH:7]=2)[C:11]1=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20680748HCID 20680748, compound

Product 1

HCID 20680715HCID 20680715, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-[1-(4-acetylamino-3-nitrobenzyl)-2-oxopyrrolidin-3-(S)-yl]-2,2,2 -trifluoroacetamide (0.65 g, 1.67 mmol) in EtOH (4 mL) is added 1 N NaOH (6 mL) solution. The yellow mixture is heated at 50° C. for 3 hours as a brown solution resulted. The reaction mixture is allowed to cool and then concentrated in vacuo. The crude residue is diluted with water and 1N NaOH 10 mL) and the aqueous phase is extracted with CHCl3 (4×50 mL). The combined organic layers are dried over anhydrous Na2SO4, filtered and concentrated to give the title compound (0.22 g, 0.88 mmol) as a yellow solid which is used as is in the subsequent step.

Workup

  1. customresulted
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. additionThe crude residue is diluted with water and 1N NaOH 10 mL) and the aqueous phase
  5. extractionis extracted with CHCl3 (4×50 mL)
  6. dry with materialThe combined organic layers are dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4349694ae4fa4ecab89defda632c9246
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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