Ethyl Acetate → HCID 19354611, compound

HRID 377564Notes

Reaction equation

HRID 377564 reaction equation
C[Mg]Br.[Cl:4][C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:32])[C:14]([N:17]2[C:22](=[O:23])[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:20]([CH:30]=[O:31])[O:19][CH2:18]2)([CH3:16])[CH3:15])[CH:8]=[C:9]([Cl:11])[CH:10]=1.[Cl-].[NH4+].[C:35](OCC)(=O)C>CCOCC.O1CCCC1>[Cl:4][C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:32])[C:14]([N:17]2[C:22](=[O:23])[C:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:20]([CH:30]([OH:31])[CH3:35])[O:19][CH2:18]2)([CH3:16])[CH3:15])[CH:8]=[C:9]([Cl:11])[CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19354584HCID 19354584, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19354611HCID 19354611, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (1.7 ml of a 3M solution in ether) was added dropwise to a stirred solution of N-(3,5-dichlorophenyl)-2-(6-formyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (1.0 g) in dry tetrahydrofuran under an inert atmosphere at -5° C. After 1 hour at that temperature, ammonium chloride solution (saturated) and ethyl acetate were added. The organic phase was washed (brine), dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica gel, eluting with dichloromethane/ethyl acetate to give N-(3,5-dichlorophenyl)-2[2,3-dihydro-6-(1-hydroxyethyl)-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl]-2-methylpropanamide (compound 123, 0.27 g) as a cream solid, m.p. 85-88° C.

Workup

  1. washThe organic phase was washed (brine)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated
  4. customThe residue was purified
  5. customby dry column chromatography on silica gel
  6. washeluting with dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-19fd9203bbfd41f08b6f156c7fa45b0e
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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