Trifluoroacetic acid → HCID 10407547, compound

HRID 1452676Notes

Reaction equation

HRID 1452676 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:21][C:22](=[O:35])[CH2:23][CH2:24][CH2:25][CH2:26][C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:4][C:3]=1[NH:21][C:22](=[O:35])[CH2:23][CH2:24][CH2:25][CH2:26][C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57526922HCID 57526922, compound

Product 1

HCID 10407547HCID 10407547, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of tert-butyl 4-{4-fluoro-3-[(6-oxo-6-phenylhexanoyl)amino]phenyl}-1-piperidine carboxylate (49.0 mg, 0.101 mmol) in CH2Cl2 (3.0 mL) was added trifluoroacetic acid (114 mg, 1.01 mmol) at room temperature. The reaction mixture was stirred for 30 min and concentrated in vacuo. The residue was dissolved in CHCl3/i-PrOH (3:1, 10 mL) and was basified to pH 11 with 5% KOH solution. The organic layer was separated and the aqueous layer was extracted with CHCl3/i-PrOH (3:1, 3×10 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford N-[2-fluoro-5-(4-piperidinyl)phenyl]-6-oxo-6-phenylhexanamide (35.5 mg, 86.0%). HCl salt: 1H NMR (400 MHz, CDCl3) δ 8.14-8.01 (br, 1H), 8.01-7.89 (m, 2H), 7.65-7.52 (m, 1H), 7.52-7.43 (m, 2H), 7.43-7.26 (br, 1H), 7.13-7.00 (m, 1H), 7.00-6.88 (br, 1H), 3.68-3.43 (m, 2H), 3.19-2.92 (br, 4H), 2.89-2.67 (m, 1H), 2.61-2.36 (br, 2H), 2.26-2.06 (m, 2H), 2.06-1.93 (m, 2H), 1.93-1.71 (br, 4H); ESMS m/e: 383.2 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CHCl3/i-PrOH (3:1, 10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CHCl3/i-PrOH (3:1, 3×10 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bac4a6eb0312494f80379765e1e4a57b
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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