Trifluoroacetic acid → HCID 22864424, compound

HRID 1078159Notes

Reaction equation

HRID 1078159 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH2:15][N:14]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[NH:36][C:37]([NH:39][CH3:40])=[O:38])=[CH:26][CH:25]=2)[C:13]1=[O:41])=O)C1C=CC=CC=1.FC(F)(F)C(O)=O>C(O)C.[Pd]>[NH2:11][C@@H:12]1[CH2:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH2:15][N:14]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[NH:36][C:37]([NH:39][CH3:40])=[O:38])=[CH:26][CH:25]=2)[C:13]1=[O:41]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22864426HCID 22864426, compound

Product 1

HCID 22864424HCID 22864424, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 310 mg (0.552 mmol) of the intermediate obtained in Step J in 5 mL of ethanol with 0.1 mL of trifluoroacetic acid was hydrogenated at 40 psi and ambient temperature in the presence of 100 mg of 10% palladium on carbon for 4 hours. The mixture was filtered through Celite and solvent removed under vacuum to give the product. 1H NMR (400 MHz, CD3OD): δ2.69 (s, 3H), 3.24 (m, 1H), 3.44 (dd; 6, 16 Hz; 1H), 4.11 (s, 2H), 4.13 (d, 17 Hz, 1H), 4.68 (d, 14 Hz, 1H), 4.86 (d, 14 Hz, 1H), 5.14 (m, 1H), 5.18 (d, 17 Hz, 1H), 6.95 (d, 8 Hz, 1H), 7.07 (t, 8 Hz, 1H), 7.15-7.25 (m, 5H), 7.28 (m, 1H), 7.28 (d, 8 Hz, 2H), 7.33 (t, 8 Hz, 1H), 7.38 (d, 8 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite and solvent
  2. customremoved under vacuum
  3. customto give the product

Sources & evidence

ORD record
ord-822dbd28c780438085ea9eabc88794a0
Source dataset
uspto-grants-1996_08
Patent number
US05545735

Reaction notes

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