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-(2-hyroxyethyl) piperazylamide

HRID 1976362Notes

Reaction equation

HRID 1976362 reaction equation
[N:1]1([CH:7](O)C)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C1([N:16]=C=NC2CCCCC2)CCCCC1.ClCCl.[O:28]1[C@@:45]2([CH3:46])[C@@H:29]1[CH2:30][C@@H:31]1[C:36]([C:37](O)=[O:38])=[CH:35][O:34][C@@H:33]([O:40][C:41](=[O:44])[NH:42][CH3:43])[C@H:32]12.ClCCl.[CH3:50][OH:51]>CN(C1C=CN=CC=1)C>[OH:51][CH2:50][CH2:7][N:1]1[CH2:2][CH2:3][N:4]([NH:16][C:37]([C:36]2[C@H:31]3[CH2:30][C@@H:29]4[O:28][C@:45]4([CH3:46])[C@@H:32]3[C@H:33]([O:40][C:41](=[O:44])[NH:42][CH3:43])[O:34][CH:35]=2)=[O:38])[CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 177695631-(Piperazin-1-yl)ethan-1-olHCID 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 acidHCID 21226129Dichloromethane methanol

Product 1

HCID 86755117(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-(2-hyroxyethyl) piperazylamideYield 49%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

0.28 ml of piperazylethanol, 273 mg of DMAP and 461 mg of dicyclohexylcarbodiimide were added to 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 followed by 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 amorphous substance 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-(2-hydroxyethyl) piperazylamide (276 mg, yield: 49%). The physicochemical properties of this compound are described in Table 5, Compound No. 22.

Workup

  1. extractionThe reaction mixture was then extracted with dichloromethane
  2. washAfter washing the organic phase with saturated aqueous sodium bicarbonate 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-a3e8c4d5db29434cbbc5283be2610048
Source dataset
uspto-grants-2001_05
Patent number
US06225478B1

Reaction notes

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