Hydrochloric Acid → (8E)-8-[[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-8-phenyloctanoic acid

HRID 2299869Notes

Reaction equation

HRID 2299869 reaction equation
[OH2:1].[OH-:2].[Li+].C(CCCC[CH2:10][CH2:11][CH2:12]/[C:13](=[N:20]\[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[S:38][CH:39]=[CH:40][CH:41]=3)[O:34][C:35]=2[CH3:36])=[CH:25][CH:24]=1)/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C.O.Cl>O1CCCC1.C(O)C>[CH3:36][C:35]1[O:34][C:33]([C:37]2[S:38][CH:39]=[CH:40][CH:41]=2)=[N:32][C:31]=1[CH2:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][O:21]/[N:20]=[C:13](/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)\[CH2:12][CH2:11][CH2:10][CH2:10][CH2:11][CH2:12][C:13]([OH:2])=[O:1])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 18379788(E)-N-[[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]methoxy]-1-phenyldecan-1-imine

Product 1

HCID 22344596(8E)-8-[[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-8-phenyloctanoic acidYield 165.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (153 mg) was added to a solution of ethyl E-8-[4-[5-methyl-2-(2-thienyl)-4-oxazolylmethoxy]benzyloxyimino]-8-phenyloctane (682 mg) in tetrahydrofuran (6 ml)-water (4 ml)-ethanol (4 ml) and stirred at room temperature for 4 hours. 1N hydrochloric acid (3.7 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 E-8-[4-[5-methyl-2-(2-thienyl)-4-oxazolylmethoxy]benzyloxyimino]-8-phenyloctanoic acid (567 mg, yield 87%) as colorless crystals. m.p. 106-108° 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-62dd5747e8414bbfa628fd1d756ff7e9
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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