Hydrochloric Acid → HCID 69422682, compound

HRID 350128Notes

Reaction equation

HRID 350128 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:36]=[CH:35][C:18]([CH2:19][N:20]2[C:24]([CH2:25][CH2:26][CH3:27])=[C:23]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH:22]=[N:21]2)=[CH:17][CH:16]=1.[OH-].[Na+].C(O)C.Cl>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][N:20]2[C:24]([CH2:25][CH2:26][CH3:27])=[C:23]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:22]=[N:21]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 69423016HCID 69423016, compound

Product 1

HCID 69422682HCID 69422682, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-5-propyl-1H-pyrazol-4-yl]propionate (210 mg), 1N aqueous sodium hydroxide solution (1 ml), ethanol (1 ml), and tetrahydrofuran (1 ml) was stirred at room temperature for 2 hours. The reaction mixture was acidified with dilute 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 crystals obtained were collected by filtration to yield 3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-5-propyl-1H-pyrazol-4-yl]propionic acid (170 mg, yield: 85%). This was recrystallized from ethyl acetate-hexane. Melting point: 158–159° 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 crystals obtained
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-0c0ac2707bf3421bbecf2160db3f15b0
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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