Chlorosuccinimide → HCID 58288318, compound

HRID 1476101Notes

Reaction equation

HRID 1476101 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)[C:9]([F:12])([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2].[Cl:21]N1C(=O)CCC1=O>C(#N)C>[NH2:19][C:15]1[CH:14]=[C:13]([CH:8]([C:9]([F:11])([F:10])[F:12])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:20])[CH:18]=[CH:17][C:16]=1[Cl:21]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 58288395HCID 58288395, compound

Product 1

HCID 58288318HCID 58288318, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

13.6 g (47.0 mmol) of (+/−)-tert-butyl-3-(3-aminophenyl)-4,4,4-trifluorobutanoate were initially charged in 100 ml of acetonitrile, and 6.28 g (47.0 mmol) of N-chlorosuccinimide were added at RT. The reaction mixture was initially stirred at 60° C. for 12 h and then allowed to stand at RT for 3 days. After concentration under reduced pressure, the residue was separated by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 100:1), and the desired target product was isolated. This gave 4.49 g of the title compound (29.5% of theory).

Workup

  1. waitto stand at RT for 3 days
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was separated by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 100:1)
  4. customthe desired target product was isolated

Sources & evidence

ORD record
ord-321a57f558424a87ac7d86750ace73e6
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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