HCID 67486557, compound → HCID 67211264, compound

HRID 1755140Notes

Reaction equation

HRID 1755140 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-6f800b55b5154a1bb52a486a1195d286
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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