Potassium Carbonate → HCID 67547652, compound

HRID 2237613Notes

Reaction equation

HRID 2237613 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]1[C:20]2[CH:19]([C:21]([OH:23])=O)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[CH3:24][NH:25][C@@H:26]1[CH:31]2[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]2)[CH2:27]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C(Cl)(Cl)Cl>[N:28]12[CH2:33][CH2:32][CH:31]([CH2:30][CH2:29]1)[C@@H:26]([N:25]([CH3:24])[C:21]([CH:19]1[C:20]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[O:12][C:13]3[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:23])[CH2:27]2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 65736Xanthene-9-carboxylic acidHCID 28596232HCID 28596232, compound

Product 1

HCID 67547652HCID 67547652, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent2×

Procedure

Oxalyl chloride (0.540 ml, 0.0062 mol) was added to a solution of 9H-xanthene-9-carboxylic acid (1.16 g, 0.0051 mol) and dimethylformamide (two drops) in 20 ml of CHCl3 (ethanol free) at ECP. The mixture was allowed to warm to room temperature under stirring and maintained 1-h at this temperature. After this time, the reaction mixture was concentrated to dryness in vacuo and the obtained residue was dissolved in CHCl3 (15 ml) and concentrated again. This procedure was repeated two times. The obtained residue was dissolved in CHCl3 and the solution cooled to 0° C. A solution of 0.865 g (0.0062 mol) of (3R)—N-methylquinuclidin-3-amine (Intermediate I-4) in 10 ml of CHCl3 was added. The mixture was allowed to warm to room temperature under stirring. After 4 hours at this temperature, the reaction mixture was treated with K2CO3 (saturated solution) and the aqueous phase was extracted with CHCl3. The organic solutions were combined and washed with K2CO3 (saturated solution) and water, dried over Na2SO4 filtered and concentrated to dryness. The obtained residue was purified by column chromatography (silica gel, CHCl3:NH4OH 99:1→CHCl3:MeOH:NH4OH 98:2:1 as eluent) to yield 900 mg (50%) of the title product.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated to dryness in vacuo
  2. dissolutionthe obtained residue was dissolved in CHCl3 (15 ml)
  3. concentrationconcentrated again
  4. dissolutionThe obtained residue was dissolved in CHCl3
  5. temperaturethe solution cooled to 0° C
  6. temperatureto warm to room temperature
  7. stirringunder stirring
  8. extractionthe aqueous phase was extracted with CHCl3
  9. washwashed with K2CO3 (saturated solution) and water
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated to dryness
  13. customThe obtained residue was purified by column chromatography (silica gel, CHCl3:NH4OH 99:1→CHCl3:MeOH:NH4OH 98:2:1 as eluent)

Sources & evidence

ORD record
ord-e4a8e4b304534c2fb737e7532bd1b2b0
Source dataset
uspto-grants-2010_05
Patent number
US07718670B2

Reaction notes

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