Ammonium formate → (RS) Methyl 3-{5-[2-(4-amino-3-hydroxy-phenyl)-acetylamino]-pyridin-2-yl}-butanoate

HRID 49720

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]([CH3:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[N:19][CH:20]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]([CH3:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[N:19][CH:20]=2)=[O:13])=[CH:3][C:2]=1[OH:1]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (RS) methyl 3-{5-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-2-yl}-butanoate (2.0 g, Reference Example 25) in ethanol (80 mL), at 60° C., was treated with ammonium formate (4.0 g) and 10% palladium on charcoal (0.5 g). After stirring at 60° C. for 1 hour the reaction mixture was cooled and then filtered. The filtrate was evaporated and the residue was dissolved in ethyl acetate. This solution was washed twice with water, then dried over magnesium sulphate and then evaporated to give the title compound (1.37 g) as an oil.

Workup

temperaturewas cooled
filtrationfiltered
customThe filtrate was evaporated
dissolutionthe residue was dissolved in ethyl acetate
washThis solution was washed twice with water
dry with materialdried over magnesium sulphate
customevaporated

Sources & evidence

ORD record: ord-c5851f05f1e04dd48d0249cc66ba9d27
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706738B2

Linked notes

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