Hydrochloric Acid → HCID 22344567, compound

HRID 584433Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A 1N aqueous saturated solution of sodium hydroxide (5 ml) was added to a solution of ethyl E-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-2-(3-pyridyl)acetate (520 mg) in tetrahydrofuran (10 ml)-methanol (5 ml) and stirred at 40° C. for 1 hour. 1N hydrochloric acid (5.5 ml) was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was recrystallized from acetone-diisopropyl ether to obtain E-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-2-(3-pyridyl)acetic acid (427 mg, yield 88%) as colorless crystals. m.p. 130-131° C. (decomposition)

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was recrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record: ord-72897e02e8bc4ea3aff6516835ebecc9
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924300B2

Reaction notes

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