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Ethyl Acetate → Gamma-secretase modulators

HRID 553960
Notes
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Reaction equation

HRID 553960 reaction equation
O.[OH-].[Li+].[O:4]=[C:5]1[N:14]2[C@H:9]([CH2:10][O:11][CH2:12][C@H:13]2[C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=2)[CH2:8][CH2:7][CH:6]1P(=O)(OCC)OCC.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1)[CH:37]=O.C(OCC)(=O)C>O1CCCC1.C(O)C.O>[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1)/[CH:37]=[C:6]1\[CH2:7][CH2:8][C@@H:9]2[N:14]([C:5]\1=[O:4])[C@H:13]([C:15]1[CH:16]=[C:17]([F:23])[C:18]([F:22])=[C:19]([F:21])[CH:20]=1)[CH2:12][O:11][CH2:10]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612713diethyl[(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonate

Product 1

HCID 24781184Gamma-secretase modulatorsYield 38.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (63.4 mg) was added to a mixed solution of diethyl [(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonate (372 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (229 mg) in tetrahydrofuran (6 mL) and ethanol (2 mL) at room temperature, and the reaction solution was stirred at room temperature for two hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine. The resulting organic layer was 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 163.2 mg of the title compound.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialThe resulting organic layer was dried 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-0ab6a1af2f6c487483d219b1035da2a7
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08048878B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes