Ethyl Acetate → HCID 24781615, compound

HRID 553999Notes

Reaction equation

HRID 553999 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[CH2:16][O:15][CH2:14][C@@H:13]3[CH2:17][CH2:18][CH:19](P(=O)(OCC)OCC)[C:20](=[O:21])[N:12]23)=[CH:7][CH:6]=1.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[N:40]1[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]1)[CH:35]=O.C(OCC)(=O)C>C1COCC1.C(O)C.O>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]2[CH2:16][O:15][CH2:14][C@@H:13]3[CH2:17][CH2:18]/[C:19](=[CH:35]\[C:34]4[CH:37]=[CH:38][C:39]([N:40]5[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]5)=[C:32]([O:31][CH3:30])[CH:33]=4)/[C:20](=[O:21])[N:12]23)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612719HCID 86612719, compound

Product 1

HCID 24781615HCID 24781615, compoundYield 80.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (13.1 mg) was added to a mixed solution of diethyl [(4R,9aS)-4-(4-chlorophenyl)-6-oxooctahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonate (73.5 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (47.5 mg) in THF (1.5 mL) and ethanol (0.5 mL) at room temperature, and the reaction solution was stirred at room temperature for 1.5 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) to obtain 68.4 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-cc4a3fdb211546d187090f48fcaba78e
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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