HCID 69422740, compound → HCID 178471113, compound

HRID 350158Notes

Reaction equation

HRID 350158 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:55]=[CH:54][C:18]([CH2:19][N:20]2[CH:24]=[C:23](/[CH:25]=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:32]CC3C=CC(OCC4N=C(C5C=CC=CC=5)OC=4C)=CC=3)=[N:21]2)=[CH:17][CH:16]=1>[C].[Pd].O1CCCC1>[OH:32][C:22]1[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:24][N:20]([CH2:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:6][C:2]=3[CH3:1])=[CH:55][CH:54]=2)[N:21]=1

Participants

4

Reactant 1

HCID 69422740HCID 69422740, compound

Product 1

HCID 178471113HCID 178471113, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl(E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]-1H-pyrazol-4-yl]propenoate (24.15 g), 5% palladium-carbon (34.22 g), and tetrahydrofuran (400 ml) was stirred at room temperature under a hydrogen atmosphere overnight. After removal of the catalyst by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-hydroxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate was obtained from the fraction eluted with ethyl acetate-hexane (2:1, volume ratio) as colorless crystals (13.93 g, yield: 92%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 137–138° C.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a31a5d2524dc4097b8be99b7adb0df73
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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