HCID 69451845, compound → HCID 69454020, compound

HRID 2229552Notes

Reaction equation

HRID 2229552 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]=[CH2:16])=[CH:9][C:8]=1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][C:21]=1[F:27])[CH3:2]>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:8]=1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:27])[CH3:2]

Participants

5

Reactant 1

HCID 69451845HCID 69451845, compound

Product 1

HCID 69454020HCID 69454020, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [4-allyloxy-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester (0.998 g, 2.35 mmol) in ethanol (150 mL) and ethyl acetate (5 mL) was degassed and put under a nitrogen atmosphere. Palladium catalyst (10% Pd-c, Degussa) was added and the flask was evacuated and treated with hydrogen (balloon). After stirring overnight, the solution was filtered through a pad of silica gel and washed with methanol. After concentrating the solution, the crude product was purified by flash collumn chromatography (30% hepatane in ethyl acetate) to give [4-propyloxy-2-(2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester.

Workup

  1. customthe flask was evacuated
  2. additiontreated with hydrogen (balloon)
  3. filtrationthe solution was filtered through a pad of silica gel
  4. washwashed with methanol
  5. concentrationAfter concentrating the solution
  6. customthe crude product was purified by flash collumn chromatography (30% hepatane in ethyl acetate)

Sources & evidence

ORD record
ord-e8828fb72c994deb9a108e782ba13cfb
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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