Acetone → HCID 59570999, compound

HRID 2192908Notes

Reaction equation

HRID 2192908 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:53])[CH:15]([C:38]1[CH:43]=[CH:42][C:41]([S:44]([CH:47]2[CH2:49][CH2:48]2)(=[O:46])=[O:45])=[C:40]([CH:50]2[CH2:52][CH2:51]2)[CH:39]=1)[CH2:16][C@H:17]1[CH2:37][CH2:36][C:19]2(O[C@H](C3C=CC=CC=3)[C@@H](C3C=CC=CC=3)[O:20]2)[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CC(C)=O.C(=O)([O-])O.[Na+]>O>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:53])[C@@H:15]([C:38]1[CH:43]=[CH:42][C:41]([S:44]([CH:47]2[CH2:49][CH2:48]2)(=[O:46])=[O:45])=[C:40]([CH:50]2[CH2:52][CH2:51]2)[CH:39]=1)[CH2:16][C@H:17]1[CH2:37][CH2:36][C:19](=[O:20])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59570886HCID 59570886, compound

Product 1

HCID 59570999HCID 59570999, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (4R)-4-benzyl-3-{2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoyl}-1,3-oxazolidin-2-one (70 g), 4 M hydrochloric acid (140 mL), and acetone (560 mL) was stirred under heating and reflux for 2 hours. After leaving it to be cooled at room temperature, saturated aqueous sodium hydrogen carbonate solution/water (1/1, 200 mL) was added thereto, and the organic solvent was evaporated under reduced pressure, followed by extraction with ethyl acetate (200 mL×2). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70→50:50) to obtain (4R)-4-benzyl-3-{(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoyl}-1,3-oxazolidin-2-one (21 g) as a colorless amorphous substance.

Workup

  1. temperatureunder heating
  2. temperaturereflux for 2 hours
  3. customAfter leaving it
  4. customthe organic solvent was evaporated under reduced pressure
  5. extractionfollowed by extraction with ethyl acetate (200 mL×2)
  6. washThe organic layer was washed with saturated brine (100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was then evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70→50:50)

Sources & evidence

ORD record
ord-834d53d969b4429dbbd41e3f3eb5a867
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

Loading…