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

HRID 584532Notes

Reaction equation

HRID 584532 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:37])=[C:9]([CH2:11][O:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][O:18]/[N:19]=[C:20](/[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)\[CH2:21][CH2:22][C:23]([O:25]C)=[O:24])=[CH:15][C:14]=2[O:35][CH3:36])[N:10]=1.C(O)C.[OH-].[Na+].Cl>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:37])=[C:9]([CH2:11][O:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][O:18]/[N:19]=[C:20](/[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)\[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:15][C:14]=2[O:35][CH3:36])[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 22344612methyl (4E)-4-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]-3-methoxyphenyl]methoxyimino]-4-phenylbutanoate

Product 1

HCID 22344608(4E)-4-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]-3-methoxyphenyl]methoxyimino]-4-phenylbutanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl E-4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxyimino]-4-phenylbutyrate (1.55 g, ethanol (10 ml) and 1N aqueous sodium hydroxide (5 ml) was stirred at room temperature for 2 hours. The reaction mixture was poured into water and acidified with 1N hydrochloric acid to give E-4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxyimino]-4-phenylbutyric acid as crystals (1.40 g, yield 93%). Recrystallization from ethanol-isopropyl ether gave colorless prisms. m.p. 131-132° C.

Sources & evidence

ORD record
ord-26aa350002ac4feb887b9778d0c66dbe
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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