Potassium Carbonate → Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate

HRID 40113

Reaction equation

HRID 40113 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:5][NH:6][C:7](=[O:15])[CH2:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].[CH2:20]([O:22][C:23](=[O:34])[C:24]1[CH:29]=[CH:28][C:27](F)=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=1)[CH3:21].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:5][NH:6][C:7](=[O:15])[CH:8]([C:27]1[CH:28]=[CH:29][C:24]([C:23]([O:22][CH2:20][CH3:21])=[O:34])=[CH:25][C:26]=1[N+:31]([O-:33])=[O:32])[C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate2×HCID 59762316HCID 59762316, compound2×

Product 1

HCID 59762433Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3,4-difluorobenzyl)-4,4-dimethyl-3-oxopentanamide (Compound 112, 126 mg, 0.47 mmol) and ethyl4-fluoro-3-nitrobenzoate (Compound 113, 100 mg, 0.47 mmol) in DMSO (1 ml) was added K2CO3 (130 mg, 0.94 mmol). The mixture was stirred at room temperature for 16 h, diluted with EtOAc, washed with 1 M HCl, H2O, and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as a yellow solid.

Workup

  1. washwashed with 1 M HCl, H2O, and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-458a7423207f404ebdf8a47f33f1bb6e
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Linked notes

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