Potassium Carbonate → 9-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-5-methoxy-9H-xanthene-3-carboxylic acid diethylamide
Reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:22]3[CH2:28][CH:27]4[N:29](C(=O)C(F)(F)F)[CH:24]([CH2:25][CH2:26]4)[CH2:23]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:36]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:22]3[CH2:23][CH:24]4[NH:29][CH:27]([CH2:26][CH2:25]4)[CH2:28]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:37]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 5-methoxy-9-[8-(2,2,2-trifluoro-acetyl)-8-aza-bicyclo[3.2.1]-oct-3ylidene]-9H-xanthene-3-carboxylic acid diethylamide, 5c (3.2g, 6.22 mmol) and potassium carbonate (1.89 g, 13.7 mmol) in methanol (50 mL) was stirred at rt overnight. The mixture was evaporated, and partitioned between methylene chloride (100 mL) and water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated, yielding 2.72 g of 9-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-5-methoxy-9H-xanthene-3-carboxylic acid diethylamide, 6c. MS m/z=419.0 (MH+).
Workup
- customThe mixture was evaporated
- custompartitioned between methylene chloride (100 mL) and water (100 mL)
- customThe organic layer was separated
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-a14745aed8454bb4bbbffd096d72d657
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589104B2
Reaction notes
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