Morpholine → HCID 23144738, compound

HRID 1967816Notes

Reaction equation

HRID 1967816 reaction equation
[CH:1]1([C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:20])OC(C)(C)C)=[N:10][C:9]=2[C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>O1CCOCC1>[CH:1]1([C:6]([C:8]2[S:12][C:11]([NH:13][C:14]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:20])=[N:10][C:9]=2[C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 23144454HCID 23144454, compound

Product 1

HCID 23144738HCID 23144738, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 432 (251 mg, 0.693 mmol) was dissolved in 1,4-dioxane (5 mL), and morpholine (6.19 mL, 70.9 mmol) was added thereto, followed by stirring overnight under heating and reflux. The reaction mixture was concentrated under reduced pressure, and water was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1) to afford the entitled Compound 435 (168 mg, 64%) as a pale brown solid.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the resulting residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a3ded42649f24367841c3c3dc96e07ff
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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