Furan, 2,5-dimethoxy- → HCID 86599415, compound

HRID 1392197Notes

Reaction equation

HRID 1392197 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][C@:9]23[CH2:16][C@H:15]([NH2:17])[CH2:14][N:13]2[C:12](=[O:18])[N:11]([C:19]2[CH:24]=[C:23]([Cl:25])[N:22]=[C:21]([Cl:26])[CH:20]=2)[C:10]3=[O:27])=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+].CO[C:39]1O[C:41](OC)=[CH:42][CH:43]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C.CCOC(C)=O>[F:31][C:2]([F:30])([F:1])[O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][C@:9]23[CH2:16][C@H:15]([N:17]4[CH:39]=[CH:43][CH:42]=[CH:41]4)[CH2:14][N:13]2[C:12](=[O:18])[N:11]([C:19]2[CH:24]=[C:23]([Cl:25])[N:22]=[C:21]([Cl:26])[CH:20]=2)[C:10]3=[O:27])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 118607Furan, 2,5-dimethoxy-HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 86599414HCID 86599414, compound

Product 1

HCID 86599415HCID 86599415, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound from Example 63 (0.25 g) in acetic acid (5 mL) was added sodium acetate (0.26 g) and 2,5-dimethoxyfuran (0.14 mL). After 20 minutes at reflux, the reaction was cooled, diluted with EtOAc, neutralized with solid NaHCO3. The organic solution was collected, washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, concentrated and purified by chromatography (silica gel; 95:5 CH2Cl2/methanol, Chromatotron) to afford the titled compound (0.145 g): MS (m/z) 525 [MH+]. mp 129.5° C.

Workup

  1. temperatureAfter 20 minutes at reflux
  2. temperaturethe reaction was cooled
  3. customThe organic solution was collected
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography (silica gel; 95:5 CH2Cl2/methanol, Chromatotron)

Sources & evidence

ORD record
ord-4a97a0da64b740578e32bd9205e2f7a5
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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