Potassium Carbonate → Tert-butyl 2-(3-nitrobenzylamino)acetate

HRID 735630Notes

Reaction equation

HRID 735630 reaction equation
C([O-])([O-])=O.[K+].[K+].FC(F)(F)C([N:11]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)=O>CO.O>[N+:19]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][NH:11][CH2:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57842799tert-butyl N-(3-nitrobenzyl)-N-(trifluoroacetyl)glycinate

Product 1

HCID 57842741Tert-butyl 2-(3-nitrobenzylamino)acetateYield 47%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

K2CO3 (1.5 g, 11 mmol) was added to a solution of 52B (800 mg, 2.2 mmol) in MeOH/H2O (2:1, 9 mL) and the mixture was refluxed for 2 h. Volatiles were removed in vacuo and the remaining aqueous mixture was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield 52C (275 mg, 47%) as a clear oil. MS (ESI) m/z 267.1 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customVolatiles were removed in vacuo
  3. extractionthe remaining aqueous mixture was extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-58d357519c404af8a24640ff4a19b0f8
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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