Ammonium formate → (RS) Methyl 3-{6-[2-(4-amino-3-hydroxy-phenyl)-acetylamino]-pyridin-3-yl}-butyrate
Reaction equation
C([O-])=O.[NH4+].[OH:5][C:6]1[CH:7]=[C:8]([CH2:15][C:16]([NH:18][C:19]2[N:24]=[CH:23][C:22]([CH:25]([CH3:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)=[O:17])[CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O>[Pd].C(O)C>[NH2:12][C:11]1[CH:10]=[CH:9][C:8]([CH2:15][C:16]([NH:18][C:19]2[N:24]=[CH:23][C:22]([CH:25]([CH3:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)=[O:17])=[CH:7][C:6]=1[OH:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
Ammonium formate (1.7 g) and 10% palladium on charcoal were added to a solution of (RS) methyl 3-{6-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-3-yl}-butanoate (180 mg, Reference Example 15) in ethanol (15 mL). The mixture was stirred at 60° C. for 1 hour, then cooled to room temperature and then filtered through a pad of diatomaceous earth. The filter pad was washed with ethanol. The combined filtrate and washings were evaporated and the residue was dissolved in ethyl acetate. This solution was washed with water, then dried over magnesium sulphate and then evaporated to give the title compound (134 mg) as a pale brown oil which was used without further purification.
Workup
- temperaturecooled to room temperature
- filtrationfiltered through a pad of diatomaceous earth
- washThe filter pad was washed with ethanol
- customThe combined filtrate and washings were evaporated
- dissolutionthe residue was dissolved in ethyl acetate
- washThis solution was washed with water
- dry with materialdried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-4bb36f5b667c4fed8088862929155d19
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706738B2
Reaction notes
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