Cesium carbonate → tert-butyl N-(3-nitrobenzyl)-N-(trifluoroacetyl)glycinate

HRID 735629Notes

Reaction equation

HRID 735629 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[F:10][C:11]([F:26])([F:25])[C:12]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)=[O:13].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[F:10][C:11]([F:25])([F:26])[C:12]([N:14]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)=[O:13]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 57842617Acetamide, 2,2,2-trifluoro-N-[(3-nitrophenyl)methyl]-

Product 1

HCID 57842799tert-butyl N-(3-nitrobenzyl)-N-(trifluoroacetyl)glycinateYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-bromoacetate was added to a solution of 52A (950 mg, 3.8 mmol) in DMF (8 mL) with Cs2CO3 (1.5 g, 4.6 mmol) and stirred 15 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (0% to 60% EtOAc in hexanes) to afford 52B (850 mg, 61%) as a clear oil. MS (ESI) m/z 361.3 (M−H)−.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (0% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bb5e8e9ff22845e481c1e6351c88857f
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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