Benzyl 3-{4-[5-(2-fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenoxy}-2,2-dimethylpropionate → 3-{4-[5-(2-Fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenoxy}-2,2-dimethylpropionic acid

HRID 2039767Notes

Reaction equation

HRID 2039767 reaction equation
[F:1][C:2]1[CH:40]=[CH:39][CH:38]=[CH:37][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[O:11][C:12]([C:14]3[CH:34]=[C:33]([CH3:35])[C:17]([O:18][CH2:19][C:20]([CH3:32])([CH3:31])[C:21]([O:23]CC4C=CC=CC=4)=[O:22])=[C:16]([CH3:36])[CH:15]=3)=[N:13][C:8]2=[CH:7][CH:6]=1>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:40]=[CH:39][CH:38]=[CH:37][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[O:11][C:12]([C:14]3[CH:15]=[C:16]([CH3:36])[C:17]([O:18][CH2:19][C:20]([CH3:32])([CH3:31])[C:21]([OH:23])=[O:22])=[C:33]([CH3:35])[CH:34]=3)=[N:13][C:8]2=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 71186253Benzyl 3-{4-[5-(2-fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenoxy}-2,2-dimethylpropionate

Product 1

HCID 711862943-{4-[5-(2-Fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenoxy}-2,2-dimethylpropionic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

50 mg of palladium on carbon (5%) were added to a solution of 150 mg (41%) of benzyl 3-{4-[5-(2-fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenoxy}-2,2-dimethylpropionate in 7.5 ml of ethyl acetate, and the mixture was hydrogenated at 5 bar for 16 h. The catalyst was filtered off and the filtrate was concentrated. This gave 100 mg (80%) of the title compound.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-277a83e28cc847f994bc707529dce678
Source dataset
uspto-grants-2013_11
Patent number
US08580816B2

Reaction notes

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