Hydrochloric Acid → HCID 11734637, compound

HRID 2299795Notes

Reaction equation

HRID 2299795 reaction equation
[H-].[Na+].[OH:3]/[N:4]=[C:5](/[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)\[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].Cl[CH2:27][C:28]1[CH:47]=[CH:46][C:31]([O:32][CH2:33][C:34]2[N:35]=[C:36]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[O:37][C:38]=2[CH3:39])=[CH:30][CH:29]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:39][C:38]1[O:37][C:36]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[N:35][C:34]=1[CH2:33][O:32][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][O:3]/[N:4]=[C:5](/[C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:17][CH:18]=2)\[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:47][CH:46]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 87950435HCID 87950435, compound

Product 1

HCID 11734637HCID 11734637, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 211 mg) was added to a solution of ethyl E-4-(hydroxyimino)-4-(4-phenoxyphenyl)butyrate(1.50 g) and 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (1.50 g) in N,N-dimethylformamide (15 ml) at room temperature under nitrogen atmosphere and stirred for 1 hour. 1N hydrochloric acid (7 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 (1:4, v/v)-eluted fraction. The crystals were recrystallized from ethyl acetate-hexane to obtain ethyl E-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-(4-phenoxyphenyl)butyrate (1.87 g, yield 66%) as colorless crystals. m.p. 118-119° 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 (1:4, v/v)-eluted fraction
  6. customThe crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-11bda592723b487189010e9c0b387c40
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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