Hydrochloric Acid → (2E)-3-[4-({4-[({4-[(E)-2-(diethoxyphosphoryl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]-2-propenoic acid

HRID 2221985Notes

Reaction equation

[CH2:1]([O:3][P:4](/[CH:9]=[CH:10]/[C:11]1[C:12]([O:22][CH2:23][C:24]2[CH:44]=[CH:43][C:27]([O:28][CH2:29][C:30]3[N:31]=[C:32](/[CH:36]=[CH:37]/[C:38]([O:40]CC)=[O:39])[O:33][C:34]=3[CH3:35])=[C:26]([O:45][CH3:46])[CH:25]=2)=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[CH2:7]([O:6][P:4](/[CH:9]=[CH:10]/[C:11]1[C:12]([O:22][CH2:23][C:24]2[CH:44]=[CH:43][C:27]([O:28][CH2:29][C:30]3[N:31]=[C:32](/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39])[O:33][C:34]=3[CH3:35])=[C:26]([O:45][CH3:46])[CH:25]=2)=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=1)([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of ethyl (2E)-3-[4-({4-[({4-[(E)-2-(diethoxyphosphoryl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]-2-propenoate (0.62 g), tetrahydrofuran (2 mL) and ethanol (2 mL) was added 1N aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture were added 1N hydrochloric acid (2 mL) and water, and the precipitated crystals were collected by filtration to give (2E)-3-[4-({4-[({4-[(E)-2-(diethoxyphosphoryl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]-2-propenoic acid as colorless crystals (0.50 g, yield 85%). Recrystallization from acetone-hexane gave colorless prism crystals. melting point: 89-90° C.

Workup

filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-c43575a8c6f1432b85a62b25dcaf76d3
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

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