Methyl Ethyl Ketone → (+/-)-cis-7-Methoxy-4,4,15-trimethyl-15,15c-dihydro-4H-benzo[b][1,3]-dioxolo[4',5':3,4]chromeno[6,5-g][1,8]naphthyridin-2,8[3aH]-dione

HRID 18037Notes

Reaction equation

HRID 18037 reaction equation
[OH:1][C@@H:2]1[C:19]2[C:18]3[N:17]([CH3:20])[C:16]4[N:15]=[C:14]5[CH:21]=[CH:22][CH:23]=[CH:24][C:13]5=[CH:12][C:11]=4[C:10](=[O:25])[C:9]=3[C:8]([O:26][CH3:27])=[CH:7][C:6]=2[O:5][C:4]([CH3:29])([CH3:28])[C@@H:3]1[OH:30].C[C:32](=[O:35])CC>C([O-])([O-])=O.[Na+].[Na+]>[CH3:27][O:26][C:8]1[C:9]2[C:10](=[O:25])[C:11]3[CH:12]=[C:13]4[CH:24]=[CH:23][CH:22]=[CH:21][C:14]4=[N:15][C:16]=3[N:17]([CH3:20])[C:18]=2[C:19]2[C@H:2]3[O:1][C:32](=[O:35])[O:30][C@H:3]3[C:4]([CH3:28])([CH3:29])[O:5][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6569Methyl Ethyl KetoneHCID 11327222(+/-)-cis-1,2-Dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7h-benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one

Product 1

HCID 11384935(+/-)-cis-7-Methoxy-4,4,15-trimethyl-15,15c-dihydro-4H-benzo[b][1,3]-dioxolo[4',5':3,4]chromeno[6,5-g][1,8]naphthyridin-2,8[3aH]-dione

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

635.62 mg of N,N′-carbonyldiimidazole are added to a solution of 200 mg of the compound of Example 3 in 90 ml of 2-butanone. The reaction mixture is refluxed for 4 days under argon and then, after cooling, diluted with an aqueous 5% Na2CO3 solution (15 ml) and extracted with ethyl acetate. The organic solutions are combined, dried over anhydrous sodium sulphate, filtered and then evaporated to dryness under reduced pressure. Chromatography on silica gel (dichloromethane and then a gradient of methanol in dichloromethane of from 0.1 to 1.5%) allow 78 mg of the expected product to be isolated.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 days under argon
  2. temperatureafter cooling
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customto be isolated

Sources & evidence

ORD record
ord-238b96d2416846d38db9e8b5e974244a
Source dataset
uspto-grants-2010_06
Patent number
US07741325B2

Reaction notes

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