Hydrochloric Acid → HCID 69214937, compound

HRID 2222029Notes

Reaction equation

HRID 2222029 reaction equation
[CH:1]([C:4]1[O:5][CH:6]=[C:7](/[CH:9]=[CH:10]/[C:11]2[C:12]([O:22][CH2:23][C:24]3[CH:49]=[CH:48][C:27]([O:28][CH2:29][C:30]4[N:31]=[C:32]([C:36]5[CH:41]=[CH:40][C:39]([CH2:42][C:43]([O:45]CC)=[O:44])=[CH:38][CH:37]=5)[O:33][C:34]=4[CH3:35])=[C:26]([O:50][CH3:51])[CH:25]=3)=[N:13][N:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:15]=2)[N:8]=1)([CH3:3])[CH3:2].O1CCCC1.[OH-].[Na+].Cl>C(O)C>[CH:1]([C:4]1[O:5][CH:6]=[C:7](/[CH:9]=[CH:10]/[C:11]2[C:12]([O:22][CH2:23][C:24]3[CH:49]=[CH:48][C:27]([O:28][CH2:29][C:30]4[N:31]=[C:32]([C:36]5[CH:37]=[CH:38][C:39]([CH2:42][C:43]([OH:45])=[O:44])=[CH:40][CH:41]=5)[O:33][C:34]=4[CH3:35])=[C:26]([O:50][CH3:51])[CH:25]=3)=[N:13][N:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:15]=2)[N:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86605931HCID 86605931, compound

Product 1

HCID 69214937HCID 69214937, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of ethyl {4-[4-({4-[({4-[(E)-2-(2-isopropyl-1,3-oxazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}acetate (180 mg), tetrahydrofuran (3 mL) and ethanol (3 mL) was added 1N aqueous sodium hydroxide solution (0.8 mL), and the mixture was stirred at 50° C. for 1 hr. 1N Hydrochloric acid was added to the reaction mixture for neutralization, and the mixture was extracted with ethyl acetate. The residue was recrystallized from ethyl acetate-hexane and the precipitated crystals were collected by filtration to give {4-[4-({4-[({4-[(E)-2-(2-isopropyl-1,3-oxazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}acetic acid (47 mg, yield 27%) as colorless crystals. melting point: 116-118° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe residue was recrystallized from ethyl acetate-hexane
  3. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-27280dd1532e484a8f5b5d6520331999
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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