Hydrochloric Acid → HCID 11135112, compound

HRID 584438Notes

Reaction equation

[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6](/[C:10](=[N:16]/[O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[N:28]=[C:29]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:30][C:31]=3[CH3:32])=[CH:21][CH:20]=2)/[C:11]([O:13]CC)=[O:12])[CH:7]=[CH:8][CH:9]=1.CO.Cl>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6](/[C:10](=[N:16]/[O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[N:28]=[C:29]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[O:30][C:31]=3[CH3:32])=[CH:23][CH:24]=2)/[C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=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-(3-bromophenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetate (430 mg) in tetrahydrofuran (10 ml)-methanol (5 ml) and stirred at 40° C. for 2 hours. 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-hexane to obtain Z-2-(3-bromophenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetic acid (370 mg, yield 91%) as colorless crystals. m.p. 181-182° 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-hexane

Sources & evidence

ORD record: ord-669f277efc13400e92c2f403b0b1e8b5
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924300B2

Reaction notes

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