Hydrochloric Acid → 3-(5-(Benzyloxy)-2-bromophenyl)-5-(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid

HRID 1486864Notes

Reaction equation

HRID 1486864 reaction equation
Cl[O-].[Na+].[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([Br:21])=[C:16](/[CH:18]=[N:19]/[OH:20])[CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:22][O:23][C:24](=[O:31])[CH2:25][C:26](=[CH2:30])[C:27]([OH:29])=[O:28].Cl>C1COCC1>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([Br:21])=[C:16]([C:18]2[CH2:30][C:26]([CH2:25][C:24]([O:23][CH3:22])=[O:31])([C:27]([OH:29])=[O:28])[O:20][N:19]=2)[CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 817914-Methyl hydrogen 2-methylenesuccinateHCID 23665760Sodium HypochloriteHCID 118292785(NE)-N-[(2-bromo-5-phenylmethoxyphenyl)methylidene]hydroxylamine

Product 1

HCID 1182928003-(5-(Benzyloxy)-2-bromophenyl)-5-(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acidYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous sodium hypochlorite solution (5%, 146 g) was added to a mixture of (E)-1-(5-(benzyloxy)-2-bromophenyl)-N-hydroxymethanimine (27.2 g), 4-methoxy-2-methylene-4-oxobutanoic acid (12.8 g), and THF (270 mL) at 0 C. The obtained mixture was stirred at 0 C for 1 hour and at room temperature overnight. To the reaction mixture, 1 M hydrochloric acid was added, followed by extraction with ethyl acetate. The extract was washed with bline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and then, the obtained residue was washed with hexane/diethyl ether to obtain the title compound (26.4 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with bline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. washthe obtained residue was washed with hexane/diethyl ether

Sources & evidence

ORD record
ord-9ebdb3df442f4cb9b47c9dfc599e473e
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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