Ethanol → HCID 69421614, compound

HRID 350167Notes

Reaction equation

HRID 350167 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][N:11]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[N:31]=[C:32]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[O:33][C:34]=3[CH3:35])=[CH:24][CH:23]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.C(O)C>Cl>[CH2:1]([O:8][C:9]1[C:13]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][N:11]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[N:31]=[C:32]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[O:33][C:34]=3[CH3:35])=[CH:24][CH:23]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23025049HCID 23025049, compound

Product 1

HCID 69421614HCID 69421614, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of ethyl 3-[3-benzyloxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (380 mg), 1 N aqueous sodium hydroxide solution (3 ml), tetrahydrofuran (3 ml), and ethanol (3 ml) was stirred at room temperature for one hour, and then diluted with 1 N hydrochloric acid (5 ml) to give colorless crystals, which were collected by filtration. This was recrystallized from ethyl acetate-hexane, to yield 3-[3-benzyloxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionic acid (300 mg, yield: 83%). Melting point: 108–109° C.

Workup

  1. customto give colorless crystals, which
  2. filtrationwere collected by filtration
  3. customThis was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6992c5ce513f40b386a0e48a79e86677
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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