Hydrochloric Acid → HCID 86589774, compound

HRID 2299788Notes

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 Z-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 ethyl acetate to obtain Z-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-2-(3-pyridyl)acetic acid (321 mg, yield 66%) as colorless crystals. m.p. 156-157° 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 ethyl acetate

Sources & evidence

ORD record: ord-aa957f30ef874deda1e601b0ab9f7e3c
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495581B1

Reaction notes

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