HCID 67486557, compound → HCID 67211264, compound

HRID 2371244Notes

Reaction equation

HRID 2371244 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:19]([O:21]CC2C=CC=CC=2)=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1>CCO.[Pt](=O)=O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]([C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)[C:19]([OH:21])=[O:20])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 67486557HCID 67486557, compound

Product 1

HCID 67211264HCID 67211264, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-[2-benzyloxycarbonyl-2-(4-bromo-phenyl)-ethyl]-benzoic acid methyl ester (0.7 g, 1.54 mmol) in EtOH (25 mL) at rt, was added platinum (IV) oxide (0.1 g) and the reaction mixture was stirred at room temperature for 3 h under H2 gas (1 atm). The reaction mixture was filtered through a celite plug, washed with ethyl acetate (50 mL) and concentrated under reduced pressure. The crude product was dried under vacuum for 3 h to afford 4-[2-(4-bromo-phenyl)-2-carboxy-ethyl]-benzoic acid methyl ester (0.51 g, 91%): 1H NMR (300 MHz, DMSO-d6): δ 12.52 (s, 1H), 7.77 (d, J=8.4 Hz, 2H), 7.48 (d, J=8.7 Hz, 2H), 7.28 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 3.93 (t, J=7.8 Hz, 1H), 3.79 (s, 3H), 3.30 (dd, J=8.4, 13.8 Hz, 1H), 3.0 (dd, J=8.1, 13.8 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through a celite plug
  2. washwashed with ethyl acetate (50 mL)
  3. concentrationconcentrated under reduced pressure
  4. dry with materialThe crude product was dried under vacuum for 3 h

Sources & evidence

ORD record
ord-91d1fdf51cdd43f193433019ede38332
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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