Chlorosuccinimide → HCID 67113516, compound

HRID 2196489Notes

Reaction equation

HRID 2196489 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:13][C:12]=2[F:24])[CH2:7][CH2:6]1)[CH3:2].[Cl:26]N1C(=O)CCC1=O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:25])[CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[C:12]([F:24])=[CH:13][C:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])=[CH:15][C:16]=2[Cl:26])[CH2:9][CH2:10]1)[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67113679HCID 67113679, compound

Product 1

HCID 67113516HCID 67113516, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.50 g of N-(4-tert-butoxycarbonyl-2-fluorophenyl)isonipecotic acid ethyl ester in 5 ml of DMF, 0.21 g of N-chlorosuccinimide was added, and the mixture was stirred at room temperature for 1 day. After the evaporation of the solvent, the residue was purified by silica gel column chromatography (eluent:hexane-EtOAc=5:1˜1:1) to obtain 0.51 g of N-(4-tert-butoxycarbonyl-2-chloro-6-fluorophenyl)isonipecotic acid ethyl ester.

Workup

  1. customAfter the evaporation of the solvent
  2. customthe residue was purified by silica gel column chromatography (eluent:hexane-EtOAc=5:1˜1:1)

Sources & evidence

ORD record
ord-6d8225b160664012bfdc65ac1507600f
Source dataset
uspto-grants-2012_12
Patent number
US08338429B2

Reaction notes

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