Hydrochloric Acid → HCID 136360062, compound

HRID 1617960Notes

Reaction equation

HRID 1617960 reaction equation
[CH3:1][O:2][CH:3]1[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([C@H:13]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])[CH2:14]/[C:15](/[C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH3:24])[CH:19]=3)=[N:16]\[OH:17])=[CH:9][CH:8]=2)[CH2:4]1.[ClH:32].C(=O)([O-])O.[Na+].[Cl-].[NH4+]>O1CCOCC1.C(OCC)(=O)C>[Cl:32][CH2:4][CH:3]([O:2][CH3:1])[CH2:6][NH:5][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:14][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([CH3:24])[CH:19]=2)=[N:16][OH:17])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 136166963HCID 136166963, compound

Product 1

HCID 136360062HCID 136360062, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-3-[4-(3-methoxy-azetidin-1-yl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime (example 270, 31 mg) in 1,4-dioxane (2 mL) was added at room temperature hydrochloric acid 4 M in 1,4-dioxane (187 μL). The reaction mixture was heated at 50° C. and stirred for 4 hours. A saturated solution of sodium hydrogencarbonate (2 mL) was added to neutralized the crude solution followed by a saturated aq. ammonium chloride solution. Ethyl acetate was added, the phases were separated and the inorganic one was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (25% to 100% ethyl acetate in n-heptane) to yield the title compound as a light yellow foam (89%), MS (ESI+): m/z=452.3 ([M+H]+).

Workup

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (25% to 100% ethyl acetate in n-heptane)

Sources & evidence

ORD record
ord-21c3cba607a1416ead7350fddf66fd54
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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