Trifluoroacetic acid → HCID 58288190, compound

HRID 1476143Notes

Reaction equation

HRID 1476143 reaction equation
C([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17](=[O:32])[CH:18]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])[C:11]=1[F:33])[C:6]([OH:8])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:18]([CH:19]([CH3:24])[C:20]([F:23])([F:21])[F:22])[C:17]([NH:16][C:12]2[C:11]([F:33])=[C:10]([CH2:9][CH2:5][C:6]([OH:8])=[O:7])[CH:15]=[CH:14][CH:13]=2)=[O:32])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67215561HCID 67215561, compound

Product 1

HCID 58288190HCID 58288190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

270 mg (0.553 mmol) of tert-butyl (+/−)-3-(3-{[2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-2-fluorophenyl) propanoic acid (diastereomer 1, Example 102A) were dissolved in 0.2 ml of dichloromethane, and 0.85 ml of trifluoroacetic acid was added at RT. The reaction mixture was stirred at RT for 4 h and then concentrated under reduced pressure. The residue was purified by preparative RP-HPLC (acetonitrile/water mixture). This gave 188 mg (78.7% of theory) of the target compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by preparative RP-HPLC (acetonitrile/water mixture)

Sources & evidence

ORD record
ord-2250ee8ee56647378c704956373b0025
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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