Sodium Bicarbonate → HCID 21941354, compound

HRID 2216555Notes

Reaction equation

HRID 2216555 reaction equation
F[B-](F)(F)F.C[O+:7]([CH3:9])[CH3:8].[N+:10]([C:13]1[CH:29]=[CH:28][C:16]([CH2:17][O:18][C:19]([N:21]2C[CH2:25][NH:24][C:23](=O)[CH2:22]2)=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11].C(=O)([O-])O.[Na+]>ClCCl>[CH3:8][O:7][CH:9]1[CH2:25][NH:24][CH2:23][CH2:22][N:21]1[C:19]([O:18][CH2:17][C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:29][CH:28]=1)=[O:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 21941454(4-Nitrophenyl)methyl 3-oxo-1-piperazinecarboxylate

Product 1

HCID 21941354HCID 21941354, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethyloxonium tetrafluoroborate (97%, 3.7 g) was added to the dry dichloromethane (120 mL) solution of 4-p-nitrobenzyloxycarbonyl-piperazin-2one (6.7 g) at room temperature and stirred for 17 hours. The reaction mixture was treated with saturated sodium hydrogen carbonate aqueous solution, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (3×100 mL), then the combined organic layer was washed with saturated sodium hydrogen carbonate aqueous solution and brine. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduce pressure and the title compound was obtained as a pale brown solid. Yield; 5.7 g, 80.6.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  3. washthe combined organic layer was washed with saturated sodium hydrogen carbonate aqueous solution and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e6884e3988fc44c8aff3574cc73cdb43
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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