Dichloromethane → HCID 86755119, compound

HRID 377084Notes

Reaction equation

HRID 377084 reaction equation
ClCCl.[CH3:4][O:5][C:6]([C:8]1[C@H:9]2[CH2:17][C@@H:16]3[O:18][C@:15]3([CH3:19])[C@@H:10]2[CH:11]([OH:14])[O:12][CH:13]=1)=[O:7].[Cl:20][CH2:21][C:22]([N:24]=[C:25]=[O:26])=[O:23]>CCCCCC.C(OCC)(=O)C>[CH3:4][O:5][C:6]([C:8]1[C@H:9]2[CH2:17][C@@H:16]3[O:18][C@:15]3([CH3:19])[C@@H:10]2[C@@H:11]([O:14][C:25](=[O:26])[NH:24][C:22](=[O:23])[CH2:21][Cl:20])[O:12][CH:13]=1)=[O:7]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 78209Chloroacetyl isocyanateHCID 57213576HCID 57213576, compound

Product 1

HCID 86755119HCID 86755119, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A dichloromethane solution containing 100 mg of a known (4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester was cooled with ice followed by addition of chloroacetylisocyanate (45 ml) and stirring for 15 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ethyl acetate eluate in the form of (1R,4aS,6S,7R,7aR)-1-(chloroacetylcarbamoyloxy)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester (137 mg, yield: 91%). The physicochemical properties of this compound are described in Table 8, Compound No. 40.

Workup

  1. temperaturewas cooled with ice
  2. extractionThe reaction mixture was then extracted with dichloromethane
  3. washAfter washing the organic phase with brine, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-24445cea31a04fff84da3732fafa7c35
Source dataset
uspto-grants-2000_02
Patent number
US06022888

Reaction notes

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