Water → HCID 58653655, compound

HRID 1676084Notes

Reaction equation

HRID 1676084 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([CH:7]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[N+:23]([O-])=O)[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:3][CH:2]=1.C([O-])=O.[NH4+].O>C(O)C.[Pd]>[NH2:23][C:15]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=1[NH:13][CH:7]([C:4]1[CH:3]=[CH:2][C:1]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:6][CH:5]=1)[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 58653674HCID 58653674, compound

Product 1

HCID 58653655HCID 58653655, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 3-(1,1′-biphenyl)-4-yl-3-(2,4-dinitroanilino)propanoate (320 mg, 760 μmol) in ethanol (3 mL) was added palladium on carbon (64 mg, 10% active Pd), ammonium formate (239 mg, 3.80 mmol) and water (1 mL). The solution was stirred at room temperature for 1.5 hour, and was then filtered through a pad of Celite®. The filter pad was washed with ethyl acetate, and the filtrate evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with dichloromethane, to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=3.44 min, MH+ 392].

Workup

  1. filtrationwas then filtered through a pad of Celite®
  2. washThe filter pad was washed with ethyl acetate
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6743e04273584093addd266d9c46850d
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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