Dichloromethane → HCID 57198356, compound

HRID 377082Notes

Reaction equation

HRID 377082 reaction equation
[CH2:1]([NH2:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].ClCCl.[CH3:11][O:12][C:13]([C:15]1[C@H:16]2[CH2:33][C@@H:32]3[O:34][C@:31]3([CH3:35])[C@@H:17]2[C@H:18]([O:21][C:22](OC2C=CC=CC=2)=[O:23])[O:19][CH:20]=1)=[O:14]>CCCCCC.C(OCC)(=O)C>[CH3:11][O:12][C:13]([C:15]1[C@H:16]2[CH2:33][C@@H:32]3[O:34][C@:31]3([CH3:35])[C@@H:17]2[C@H:18]([O:21][C:22](=[O:23])[NH:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[O:19][CH:20]=1)=[O:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8102HexylamineHCID 57009109HCID 57009109, compound

Product 1

HCID 57198356HCID 57198356, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

0.11 ml of n-hexylamine were added to a dichloromethane solution containing 246 mg 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 described in Example 10 followed by stirring for 1 hour 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 (1S,4aS,6S,7R,7aR)-6,7-epoxy-1-(n-hexylcarbamoyloxy)-1,4a,5,6,7,7a-hexahydro-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester (87 mg, yield: 35%). The physicochemical properties of this compound are described in Table 7, Compound No. 33.

Workup

  1. extractionThe reaction mixture was then extracted with dichloromethane
  2. washAfter washing the organic phase with 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-905adbfb08964f1fa9a26771b2a6c685
Source dataset
uspto-grants-2000_02
Patent number
US06022888

Reaction notes

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