Trifluoroacetic acid → HCID 10341054, compound

HRID 1452667Notes

Reaction equation

HRID 1452667 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10](=[O:23])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:4][C:3]=1[CH:24]1[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]1.FC(F)(F)C(O)=O>ClCCl>[F:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:4][C:5]=1[NH:9][C:10](=[O:23])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57526943HCID 57526943, compound

Product 1

HCID 10341054HCID 10341054, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of tert-butyl 4(2,4-difluoro-5-{[5-(2-methoxyphenyl)pentanoyl]amino}phenyl)-1-piperidinecarboxylate (310 mg, 0.620 mmol) in dichloromethane (5.00 mL) at 0° C. was slowly added trifluoroacetic acid (707 mg, 6.20 mmol). The reaction mixture was stirred at room temperature for 10 min and concentrated in vacuo. The residue was dissolved in i-PrOH/CHCl3 (1:3, 10 mL) and basified to pH 11 with 10% KOH solution, washed with H2O, followed by brine. The organic layer was separated, dried over MgSO4 and concentrated in vacuo to afford the desired product (108 mg, 43.3%). 1H NMR (400 MHz, CDCl3) δ 7.59 (t, 1H, J=8.2 Hz), 7.10-6.96 (m, 2H), 6.90-6.68 (m, 3H), 3.67 (s, 3H), 3.09 (d, 2H, J=12.4 Hz), 2.89 (tt, 1H, J=11.8 Hz), 2.69 (dt, 2H, J=2.6, 12.4 Hz), 2.54 (t, 2H, J=7.2 Hz), 2.33 (t, 2H, J=7.2 Hz), 1.76-1.48 (m, 8H); ESMS m/e: 403.3 (M+H)+.

Workup

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in i-PrOH/CHCl3 (1:3, 10 mL)
  4. washwashed with H2O
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09d480b5d80a4ff39d63bf16e04851b4
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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