Dichloromethane → (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 4-methylpiperazylamide

HRID 1976363Notes

Reaction equation

HRID 1976363 reaction equation
ClCCl.[O:4]1[C@@:21]2([CH3:22])[C@@H:5]1[CH2:6][C@@H:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][O:10][C@@H:9]([O:16][C:17](=[O:20])[NH:18][CH3:19])[C@H:8]12.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.[Cl-].ClC1N(C)CC[NH+:33]1C>ClCCl.CO.C(N(CC)CC)C>[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([NH:33][C:13]([C:12]2[C@H:7]3[CH2:6][C@@H:5]4[O:4][C@:21]4([CH3:22])[C@@H:8]3[C@H:9]([O:16][C:17](=[O:20])[NH:18][CH3:19])[O:10][CH:11]=2)=[O:15])[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 531671-MethylpiperazineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 18397301(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

Product 1

HCID 86755118(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 4-methylpiperazylamideYield 50%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A dichloromethane solution containing 400 mg 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 described in Example 1 was cooled with ice followed by addition of 0.20 ml of 1-methylpiperazine, 2 ml of triethylamine and 301 mg of 2-chloro-1,3-dimethylimidazolinium chloride and stirring for 15 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with saturated aqueous sodium bicarbonate 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 dichloromethane-methanol 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 4-methylpiperazylamide (264 mg, yield: 50%). The physicochemical properties of this compound are described in Table 5, Compound No. 20.

Workup

  1. temperaturewas cooled with ice
  2. extractionThe reaction mixture was then extracted with dichloromethane
  3. washAfter washing the organic phase with saturated aqueous sodium bicarbonate and 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-246b61cfcce94d35b5902606d31bbf71
Source dataset
uspto-grants-2001_05
Patent number
US06225478B1

Reaction notes

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