Dichloromethane → HCID 57009109, compound

HRID 1976364Notes

Reaction equation

HRID 1976364 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1C([O-])=O.ClCCl.[CH3:14][O:15][C:16]([C:18]1[C@H:19]2[CH2:27][C@@H:26]3[O:28][C@:25]3([CH3:29])[C@@H:20]2[CH:21]([OH:24])[O:22][CH:23]=1)=[O:17].CCCCCC.[C:36]([O:39]CC)(=[O:38])C>CN(C1C=CN=CC=1)C>[CH3:14][O:15][C:16]([C:18]1[C@H:19]2[CH2:27][C@@H:26]3[O:28][C@:25]3([CH3:29])[C@@H:20]2[C@H:21]([O:24][C:36]([O:39][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:38])[O:22][CH:23]=1)=[O:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 4368810Benzoic acid, 2-chloro-, ion(1-)HCID 21226206Ethyl acetate hexaneHCID 57213576HCID 57213576, compound

Product 1

HCID 57009109HCID 57009109, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

1.2 g of DMAP and 0.9 ml of chlorophenylformate were added to a dichloromethane solution containing 1.12 g 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 followed by stirring for 1 hour at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with dilute hydrochloric acid and 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 (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(phenoxycarbonyloxy) cyclopenta [c] pyrane-4-carboxylic acid methylester (1.16 g, yield: 70%). The physicochemical properties of this compound are as shown below.

Workup

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

Sources & evidence

ORD record
ord-d4fa0721b3fd4813babebc55f51918fd
Source dataset
uspto-grants-2001_05
Patent number
US06225478B1

Reaction notes

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