HCID 66887430, compound → HCID 10070708, compound

HRID 253359Notes

Reaction equation

HRID 253359 reaction equation
[CH2:1]([C:3](=[CH:7][CH2:8][O:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])[CH2:11]1)[C:4]([OH:6])=[O:5])[CH3:2].[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([CH:3]([CH2:7][CH2:8][O:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])[CH2:11]1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 66887430HCID 66887430, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10070708HCID 10070708, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.3 g of the 2-ethyl-4-{(1R,3S)-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]-cyclohexyloxy}but-2-enoic acid is dissolved in a solvent mixture of 2 ml of ethyl acetate and 1 ml of methanol, and 0.05 g of palladium (10% on carbon) is added. The mixture is then hydrogenated at a hydrogen pressure of 1 bar for 3 h. After removal of the palladium by filtration, the solvent mixture is removed under reduced pressure and the residue is recrystallized from acetonitrile. This gives 0.25 g of 2-ethyl-4-{(1R,3S)-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]-cyclohexyloxy}butanoic acid as a white solid. C23H30FNO5 (419.49), MS (ESI): 420 (M+H+)

Workup

  1. additionis added
  2. customAfter removal of the palladium
  3. filtrationby filtration
  4. customthe solvent mixture is removed under reduced pressure
  5. customthe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-f73ef6af2b9c4291b205cc8dbcffca2e
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

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