Hydrochloric Acid → HCID 22344567, compound

HRID 2299789Notes

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-2b22eec57f2e4078bd4a0e3be1ad89ca
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495581B1

Reaction notes

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