Phosphate → HCID 22847897, compound

HRID 1655704Notes

Reaction equation

HRID 1655704 reaction equation
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]([N:9]1[CH2:13][CH2:12][O:11][C:10]1=[O:14])=[O:8])=[O:4].[CH3:15][S:16][C:17]#[CH:18].P([O-])([O-])([O-])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C@H:5]1[C@H:6]([C:7]([N:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])=[O:8])[C:17]([S:16][CH3:15])=[CH:18]1)=[O:4]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 139101MethylthioacetyleneHCID 11769493HCID 11769493, compound

Product 1

HCID 22847897HCID 22847897, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 200 mg of powdery Molecular Sieves 4A, which had been dried by heating, were added 0.41 ml (0.050 mmol) of the toluene solution obtained above, 1.5 ml of toluene and 2 ml of petroleum ether (boiling point: ca. 80° C.) in an argon atmosphere. Further, 100.15 mg (0.502 mmol) of 3-[(E)-3-(methoxycarbonyl)propenoyl]-oxazolidin-2-one was added thereto and the mixture was cooled to 0° C. To the obtained suspension was added 135 mg (1.88 mmol) of 1-methylthioacetylene dissolved in 1.5 ml of petroleum ether. Next, the mixture was stirred at the same temperature for 24 hours. Then a 0.2M phosphate buffer solution (pH 7.0) was added to the reaction mixture to thereby cease the reaction. After filtering off inorganic matters with Celite, organic matters were extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of common salt and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by thin layer chromatography (ethyl acetate:hexane=1:1, v/v). Thus 113 mg (83%) of (-)-(3R,4R)-3-methoxycarbonyl- 1-methylthio-4-(oxazolidin-2-on-3-yl)carbonyl-1-cyclobutene was obtained. The optical purity of this compound determined by the method as will be described in Referential Example exceeded 98% ee.

Workup

  1. dry with materialTo 200 mg of powdery Molecular Sieves 4A, which had been dried
  2. temperatureby heating
  3. customthe reaction
  4. filtrationAfter filtering off inorganic matters with Celite, organic matters
  5. extractionwere extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent under reduced pressure
  9. customthe residue was purified by thin layer chromatography (ethyl acetate

Sources & evidence

ORD record
ord-8949fdede56e4688969d0237ebe41843
Source dataset
uspto-grants-1993_10
Patent number
US05250697

Reaction notes

Loading…