Acetonitrile → HCID 57124693, compound

HRID 377083Notes

Reaction equation

HRID 377083 reaction equation
C(#N)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[CH:11]([OH:14])[O:12][CH:13]=1)=[O:7].C(N(CC)CC)C.[CH3:27][N:28]=[C:29]=[O:30]>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:29](=[O:30])[NH:28][CH3:27])[O:12][CH:13]=1)=[O:7]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 57213576HCID 57213576, compound

Product 1

HCID 57124693HCID 57124693, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

An acetonitrile solution containing 790 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 0.54 ml of triethylamine and 0.23 ml of methylisocyanate and stirring for 15 hours at room temperature. The reaction mixture was then extracted with ethyl acetate. 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 (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]pyrane-4-carboxylic acid methylester (610 mg, yield: 61.7%). The physicochemical properties of this compound are described in Table 1, Compound No. 3.

Workup

  1. temperaturewas cooled with ice
  2. extractionThe reaction mixture was then extracted with ethyl acetate
  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-169993d646e3470ba480616b30c289d3
Source dataset
uspto-grants-2000_02
Patent number
US06022888

Reaction notes

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