Hydrochloric Acid → HCID 9958519, compound

HRID 2299857Notes

Reaction equation

HRID 2299857 reaction equation
O.[OH-].[Li+].[CH3:4][C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:16][O:17][C:18]1[CH:44]=[CH:43][C:21]([CH2:22][O:23]/[N:24]=[C:25](\[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)/[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[CH:20][CH:19]=1.O.Cl>O1CCCC1.CO>[CH3:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:7][C:6]=1[CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][O:23]/[N:24]=[C:25](\[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)/[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86589799HCID 86589799, compound

Product 1

HCID 9958519HCID 9958519, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (159 mg) was added to a solution of ethyl Z-8-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-8-phenyloctanoate (340 mg) in tetrahydrofuran (6 ml)-water (4 ml)-methanol (4 ml) and stirred at room temperature for 1 hour. 1N hydrochloric acid (3.8 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-8-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-8-phenyloctanoic acid (293 mg, yield 91%) as colorless crystals. m.p. 88-89° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-722514b41a464c3e857c96065e7ef438
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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