Phosphate → HCID 14507379, compound

HRID 1655706Notes

Reaction equation

HRID 1655706 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[C@H:23]([CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22](SC)=[CH:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])([O-])([O-])=[O:46]>O.CN(C=O)C.CC(C)=O>[Si:26]([O:25][CH2:24][C@H:23]1[C@H:20]([CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:21][C:22]1=[O:46])([C:39]([CH3:40])([CH3:41])[CH3:42])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 2

HCID 1061PhosphateHCID 54470910HCID 54470910, compound

Product 1

HCID 14507379HCID 14507379, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 6228DimethylformamideCatalystHCID 180AcetoneSolvent

Procedure

To 29.00 mg of cupric oxide (CuO) and 42.65 mg of cupric chloride (CUCl2) were added 5 ml of acetone, one drop of distilled water and two drops of DMF. To the suspension thus obtained was added 44 mg of (-)-(3R,4R)-3,4-bis(t-butyldiphenylsilyloxymethyl)-1-methylthio-1-cyclobutene. After stirring the obtained mixture at 30° to 40° C. for 6 hours, 24.25 mg of cupric oxide (CuO) and 88.75 mg of cupric chloride (CuCl2) were further added thereto. The obtained mixture was stirred at 30° to 40° C. for 5 hours. Then a phosphate buffer solution was added to the reaction mixture. After filtering through Celite, water was added thereto, followed by extracting with ether. The ether 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. Thus 30.40 mg of (-)-(2R,3R)-2,3-bis(t-butyldiphenylsilyloxymethyl)-1-cyclobutanone was obtained. [α]D =-13.8° (c 0.608, CH2Cl2)

Workup

  1. customTo the suspension thus obtained
  2. stirringThe obtained mixture was stirred at 30° to 40° C. for 5 hours
  3. filtrationAfter filtering through Celite, water
  4. additionwas added
  5. extractionby extracting with ether
  6. extractionThe ether extract
  7. washwas washed with a saturated aqueous solution of common salt
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationAfter distilling off the solvent under reduced pressure
  10. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-71d811b5b68a40f69a5c3f1e9818ad6d
Source dataset
uspto-grants-1993_10
Patent number
US05250697

Reaction notes

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