Trifluoroacetic acid → 3-(4-Chloro-3-{[4,4,4-trifluoro-3-methyl-2-(4-methylpiperidin-1-yl)butanoyl]amino}phenyl)propanoic acid

HRID 626455Notes

Reaction equation

HRID 626455 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=[CH:4][C:3]=1[NH:17][C:18](=[O:33])[CH:19]([N:26]1[CH2:31][CH2:30][CH:29]([CH3:32])[CH2:28][CH2:27]1)[CH:20]([CH3:25])[C:21]([F:24])([F:23])[F:22].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[NH:17][C:18](=[O:33])[CH:19]([N:26]1[CH2:27][CH2:28][CH:29]([CH3:32])[CH2:30][CH2:31]1)[CH:20]([CH3:25])[C:21]([F:24])([F:23])[F:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118106789tert-Butyl 3-(4-chloro-3-{[4,4,4-trifluoro-3-methyl-2-(4-methylpiperidin-1-yl)butanoyl]amino}phenyl)propanoate

Product 1

HCID 725468553-(4-Chloro-3-{[4,4,4-trifluoro-3-methyl-2-(4-methylpiperidin-1-yl)butanoyl]amino}phenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

45.0 mg (0.092 mmol) of tert-butyl 3-(4-chloro-3-{[4,4,4-trifluoro-3-methyl-2-(4-methylpiperidin-1-yl)butanoyl]amino}phenyl)propanoate (racemic diastereomer mixture) were dissolved in 0.1 ml of dichloromethane, and 0.35 ml of trifluoroacetic acid was added at RT. The reaction mixture was stirred at RT overnight and then concentrated under reduced pressure. The crude product was purified by preparative RP-HPLC (mobile phase acetonitrile/water). This gave 39.0 mg of the target product as a diastereomer mixture (97.9% of theory).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by preparative RP-HPLC (mobile phase acetonitrile/water)

Sources & evidence

ORD record
ord-fef0bfbe347a4af582da008852883037
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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