Hydrochloric Acid → methyl (4E)-4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methoxyimino]-4-phenylbutanoate

HRID 1070124Notes

Reaction equation

HRID 1070124 reaction equation
[H-].[Na+].[OH:3]/[N:4]=[C:5](/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)\[CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].Cl[CH2:19][C:20]1[CH:40]=[CH:39][C:23]([O:24][CH2:25][CH2:26][C:27]2[N:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:30][C:31]=2[CH3:32])=[CH:22][CH:21]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:32][C:31]1[O:30][C:29]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[N:28][C:27]=1[CH2:26][CH2:25][O:24][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][O:3]/[N:4]=[C:5](/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)\[CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:40][CH:39]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 118095944-[2-(4-Chloromethylphenoxy)ethyl]-5-methyl-2-phenyloxazoleHCID 12137371methyl (4E)-4-hydroxyimino-4-phenylbutanoate

Product 1

HCID 10983890methyl (4E)-4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methoxyimino]-4-phenylbutanoateYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 134 mg) was added to a solution of methyl E-4-(hydroxyimino)-4-phenylbutyrate (632 mg) and 4-[2-(4-chloromethylphenoxy)ethyl]-5-methyl-2-phenyloxazole (1.00 g) in N,N-dimethylformamide (10 ml) at room temperature under nitrogen atmosphere and stirred for 1 hour. 1N hydrochloric acid (5 ml) was added, an aqueous saturated solution of sodium bicarbonate was added 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 subjected to silica gel chromatography to obtain crystals from an ethyl acetate-hexane (1:3, v/v)-eluted fraction. The crystals were recrystallized from ethyl acetate-hexane to obtain methyl E-4-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyloxyimino]-4-phenylbutyrate (650 mg, yield 43%) as colorless crystals. m.p. 73-74° 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. customto obtain crystals from an ethyl acetate-hexane (1:3, v/v)-eluted fraction
  6. customThe crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-bb53c245b2964767b8495b51685a16a2
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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