Hydrochloric Acid → HCID 69421616, compound

HRID 350119Notes

Reaction equation

HRID 350119 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][N:11]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]4[N:31]=[C:32]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[O:33][C:34]=4[CH3:35])=[CH:24][CH:23]=3)[N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].C(O)C.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][N:11]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]4[N:31]=[C:32]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[O:33][C:34]=4[CH3:35])=[CH:24][CH:23]=3)[N:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 23025001HCID 23025001, compound

Product 1

HCID 69421616HCID 69421616, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[3-(4-methoxyphenyl)-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (450 mg), 1N aqueous sodium hydroxide solution (2 ml), ethanol (3 ml), and tetrahydrofuran (3 ml) was stirred at room temperature for 1 hour. The reaction mixture was acidified with 1N hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The colorless crystals obtained were collected by filtration to yield 3-[3-(4-methoxyphenyl)-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionic acid (350 mg, yield: 81%). This was recrystallized from ethyl acetate-hexane. Melting point: 137–138° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe colorless crystals obtained
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-ff07a597266a441c8ed9f75cac379187
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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