Trifluoroacetic acid → HCID 53628858, compound

HRID 2065491Notes

Reaction equation

HRID 2065491 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][CH:16]([NH:31][C:32](=[O:46])[CH:33]([N:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]1=[O:45])[CH3:34])[C:17](=[O:30])[CH2:18][O:19][C:20](=[O:29])[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28])=[O:14])(C)(C)C>ClCCl>[C:13]([CH2:15][CH:16]([NH:31][C:32](=[O:46])[CH:33]([N:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]1=[O:45])[CH3:34])[C:17](=[O:30])[CH2:18][O:19][C:20](=[O:29])[C:21]1[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=1[Cl:27])([OH:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53628860HCID 53628860, compound

Product 1

HCID 53628858HCID 53628858, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (2 ml) was added to a stirred ice cold solution of 2,6-dichloro-benzoic acid 4-tert-butoxycarbonyl-2-oxo-3-[2-(1-oxo-1H-isoquinolin-2-yl)-propionylamino]-butyl ester (110 mg, 0.19 mmol) in anhydrous dichloromethane (2 ml). The mixture was stirred at 0° C. for 1 h and at room temperature for 0.5 h. The reaction mixture was concentrated under reduced pressure and then the residue was redissolved in dry dichloromethane. This process was repeated several times in order to remove excess trifluoroacetic acid. The residue was then lyophilized twice from HPLC grade water and then purified by reverse phase HPLC using a gradient eluent of 10:90 CH3CN:water to 100:0 CH3CN:water to afford the title compound as white solid (17 mg, 16%): IR (solid) 3295, 1736, 1648, 1618, 1590 cm−1; 1H NMR (400 MHz, DMSO) 1.57 (3H, 2×d), 2.64-2.80 (2H, m), 4.73 (1H, m), 5.14-5.33 (2H, m), 5.44-5.53 (1H, m), 6.67 (1H, m), 7.44-7.74 (7H, m), 8.20 (1H, d), 8.77-8.83 (1H, bd); 13C NMR (100 MHz, DMSO) 16.72, 16.90, 53.77, 105.36, 105.49, 125.48, 126.37, 126.90, 127.49, 128.85, 130.52, 130.67, 131.15, 132.47, 132.82, 132.93, 137.09, 137.12, 161.38, 163.56, 163.64, 171.15, 171.25; MS (FAB+ve, HR) Calculated for C24H20Cl2N2O7 (MH+) 519.0726, found 519.0701.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was redissolved in dry dichloromethane
  3. customto remove excess trifluoroacetic acid
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-4560fd518a134ec0a64b8e7575159a98
Source dataset
uspto-grants-2012_10
Patent number
US08288537B2

Reaction notes

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