Trifluoroacetic acid → HCID 67186276, compound

HRID 735849Notes

Reaction equation

HRID 735849 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)[C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([O:19][C:17](=[O:18])[C:16]([N:15]([CH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)[CH2:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67188093HCID 67188093, compound

Product 1

HCID 67186276HCID 67186276, compoundYield 176%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-({{[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl}[ethoxy(oxo)acetyl]-amino}methyl)benzoic acid (5.80 g, 12.93 mmol) in DCM (150 mL) was added TFA (9.90 mL) and the resulting reaction mixture was stirred at rt for 3 h, evaporated under vacuum to give the title compound as a pink oil (7.93 g, 99.9%). 1H NMR (DMSO-d6, 300 MHz) δ 8.7 (m, 1H), 8.39 (m, 1H), 7.96 (d, 1H, J=8.3 Hz), 7.94 (d, 1H, J=8.3 Hz), 7.39 (d, 1H, J=8.3 Hz), 7.37 (d, 1H, J=8.3 Hz), 4.64 (s, 1H), 4.58 (s, 1H), 4.33 (q, 0.9H, J=7.2 Hz), 4.23 (q, 1.1H, J=7.2 Hz), 3.33-3.22 (m, 2H), 3.18 (d, 1H, J=7.6 Hz), 3.10 (d, 1H, J=7.2 Hz), 2.90-2.69 (m, 2H), 1.98 (m, 1H), 1.40-1.21 (m, 3H), 1.16 (t, 2H, J=7.1 Hz). HPLC (Condition A), Rt: 1.87 min (HPLC purity 98.9%).

Workup

  1. customthe resulting reaction mixture
  2. customevaporated under vacuum

Sources & evidence

ORD record
ord-5adfa033c72140669b92f9e73a28613a
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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