Hydrochloric Acid → HCID 69421737, compound

HRID 350122Notes

Reaction equation

HRID 350122 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])=[CH:11][N:10]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]4[N:30]=[C:31]([C:35]5[O:36][CH:37]=[CH:38][CH:39]=5)[O:32][C:33]=4[CH3:34])=[CH:23][CH:22]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].C(O)C.Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:11][N:10]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]4[N:30]=[C:31]([C:35]5[O:36][CH:37]=[CH:38][CH:39]=5)[O:32][C:33]=4[CH3:34])=[CH:25][CH:26]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 17930183HCID 17930183, compound

Product 1

HCID 69421737HCID 69421737, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[3-(4-fluorophenyl)-1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (350 mg), 1N aqueous sodium hydroxide solution (2 ml), ethanol (4 ml), and tetrahydrofuran (4 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 colorless crystals obtained were collected by filtration to yield 3-[3-(4-fluorophenyl)-1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionic acid (150 mg, yield: 45%). This was recrystallized from ethyl acetate-hexane. Melting point: 125–126° 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-8ef0f1c743a34d47956cac14a9def5a8
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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