Trifluoroacetic acid → HCID 86598170, compound

HRID 458452Notes

Reaction equation

HRID 458452 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[C:16]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:17]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:18]=1[C:19](OCC)=[O:20])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:44][C:41]1[CH:42]=[CH:43][C:38]([CH2:37][CH2:36][C:15]2[C:16]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:17]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[C:18]3[C:19](=[O:20])[N:8]4[C@@H:9]([CH2:10][CH2:11][CH2:12]4)[C:13]=3[N:14]=2)=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69516001HCID 69516001, compound

Product 1

HCID 86598170HCID 86598170, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the flask containing crude diethyl 2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-6-[2-(4-fluorophenyl)ethyl]-4-(4-methylphenyl)-1,4-dihydro-3,5-pyridinedicarboxylate (B, 1.0 mmol), 14.2 ml premixed trifluoroacetic acid and dichloromethane (10 ml/4.2 ml) were added. The resulting mixture was stirred at room temperature for 20 minutes. The solvents were removed in vacuo. The resulting residue was dissolved in a 30 ml mixture of triethylamine and dichloromethane (10 ml/20 ml) and was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with water, brine subsequently. After removing the solvent, the residue was purified with flash chromatography. 125 mg of solid was obtained. 1H NMR (400 MHz, CDCl3) δ 7.22 (m, 4H), 7.18 (t, 2H), 6.95 (t, 2m), 4.64 (m, 1H), 4.02 (q, 2H), 3.70 (m, 1H) 3.35 (m, 1H), 3.15 (m, 2H), 3.05 (m, 2H), 2.42 (m, 1H), 2.35 (s, 3H), 2.30 (m, 2H), 1.38 (m, 1H) ppm. ESI-MS m/z 459 (M+H)+, 917 (2M+1)+.

Workup

  1. additionwere added
  2. customThe solvents were removed in vacuo
  3. dissolutionThe resulting residue was dissolved in a 30 ml mixture of triethylamine and dichloromethane (10 ml/20 ml)
  4. stirringwas stirred at room temperature for 2 hours
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washwashed with water, brine subsequently
  7. customAfter removing the solvent
  8. customthe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-78a7d83f3dcd40b6b1ece52174891d05
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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