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

HRID 584530Notes

Reaction equation

HRID 584530 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:39][CH3:40])[C:24]=1[O:25][CH2:26][C:27]1[N:28]=[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:30][C:31]=1[CH3:32])[CH2:6][O:7]/[N:8]=[C:9](/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)\[CH2:10][CH2:11][C:12]([O:14]C)=[O:13].CO.[OH-].[Na+].Cl>O.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:39][CH3:40])[C:24]=1[O:25][CH2:26][C:27]1[N:28]=[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:30][C:31]=1[CH3:32])[CH2:6][O:7]/[N:8]=[C:9](/[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)\[CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 22344619methyl (4E)-4-[[3,5-dimethoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate

Product 1

HCID 22344641(4E)-4-[[3,5-dimethoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoic acidYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl E-4-[3,5-dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyrate (970 mg), methanol (5 ml), tetrahydrofuran (10 ml) and 1N aqueous sodium hydroxide (5 ml) was stirred at room temperature for 1 hour. The reaction mixture was poured into water, acidified with 2N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4), and concentrated to give E-4-[3,5-dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyric acid (880 mg, yield 93%) as crystals. Recrystallization from ethyl acetate-isopropyl ether gave colorless needles. m.p. 89-90° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ed84c9dbfbf4412e99e125f98d22808f
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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