Benzyl acetate → HCID 57974088, compound

HRID 1866616Notes

Reaction equation

HRID 1866616 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[NH:14][C:13](=[O:15])[CH2:12][S:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].[Na+].[C:18]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:20])[CH3:19]>C1COCC1>[F:8][C:6]1[CH:5]=[C:4]([C@@H:9]2[CH2:10][S:11][CH2:12][C:13](=[O:15])[N:14]2[CH2:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 8785Benzyl acetateHCID 24758Sodium hydrideHCID 57974029HCID 57974029, compound2×

Product 1

HCID 57974088HCID 57974088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of (5R)-5-(3,5-difluorophenyl)thiomorpholin-3-one (247 mg, 1.08 mmol, prepared by analogy to Intermediate 2) in THF (8.0 mL) was added sodium hydride (38 mg, 1.5 mmol, 95% by weight). After 5 minutes, the ice bath was removed and the reaction was allowed to warm to ambient temperature. Once hydrogen gas evolution had ceased, as judged by an oil bubbler, the reaction mixture was cooled to 0° C., prior to the introduction of benzyl acetate (272 mg, 1.19 mmol). After 5 minutes, the ice bath was removed and the reaction was stirred for 15 hours. The bulk of the THF was removed under reduced pressure. The residue was then diluted with water and ether. The aqueous layer was extracted once with ether and the combined organics were washed with saturated brine. The organics were then dried over sodium sulfate, filtered, and concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of MeOH:DCM—0.5:99.5 to 5:95, to give the title compound. MS: m/z=378 (M+1).

Workup

  1. customthe ice bath was removed
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. waitAfter 5 minutes
  4. customthe ice bath was removed
  5. customThe bulk of the THF was removed under reduced pressure
  6. additionThe residue was then diluted with water and ether
  7. extractionThe aqueous layer was extracted once with ether
  8. washthe combined organics were washed with saturated brine
  9. dry with materialThe organics were then dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give a residue that
  13. customwas purified by silica gel chromatography
  14. washeluting with a gradient of MeOH

Sources & evidence

ORD record
ord-2174731849b24f8e87be21fe850f3bde
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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