Potassium Sodium Tartrate → HCID 57833588, compound
Reaction equation
C[O:2][C:3]([C:5]1[C:18]2[O:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[C:19]3[CH2:25][CH:24]4[N:26](C(=O)C(F)(F)F)[CH:21]([CH2:22][CH2:23]4)[CH2:20]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[CH:21]12[NH:26][CH:24]([CH2:23][CH2:22]1)[CH2:25][C:19](=[C:10]1[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH2:3][OH:2])[C:18]=3[O:17][C:16]3[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:20]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 9-[8-(2,2,2-trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-4-carboxylic acid methyl ester in methylene chloride (0.001 to 1 M solution) at −78° C. may be treated with diisobutyl aluminum hydride (1M in cyclohexane; 2 to 10 equiv), and the mixture may be allowed to slowly warm up to 0° C. After stirring at that temperature for a period of 1 to 5 hr, an aqueous solution of Rochelle's salt may be added. The mixture may be extracted with an appropriate organic solvent such as ethyl acetate, and the organic layer may be dried over a suitable drying agent such as potassium carbonate. After filtration and evaporation, the residue may be purified via reverse phase column chromatography to yield Compound 2e.
Workup
- extractionThe mixture may be extracted with an appropriate organic solvent such as ethyl acetate
- dry with materialthe organic layer may be dried over a suitable drying agent such as potassium carbonate
- filtrationAfter filtration and evaporation
- customthe residue may be purified via reverse phase column chromatography
Sources & evidence
- ORD record
- ord-a747c5c83e864d11bd6c0f1a7ec166df
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582650B2
Reaction notes
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