Ammonium formate → HCID 58653652, compound

HRID 1676077Notes

Reaction equation

HRID 1676077 reaction equation
[N+:1]([C:4]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:5]=1[NH:6][C@@H:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][C:9]([O:11][CH3:12])=[O:10])([O-])=O.C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:1][C:4]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:5]=1[NH:6][C@@H:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 58653700HCID 58653700, compound

Product 1

HCID 58653652HCID 58653652, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl (3R)-3-(2,4-dinitroanilino)-3-phenylpropanoate (3.14 g, 9.1 mmol) in a mixture of ethanol (100 mL) and water (10 mL) was added ammonium formate (2.3 g, 36 mmol) and palladium on carbon (300 mg, 10% w/w Pd). The mixture was stirred at room temperature for 2 hours, then filtered through a pad of Celite®, evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (95:5), to afford the title compound, [LCMS (Method C, Mobile Phase I) RT=2.94 mins, MH+ 316].

Workup

  1. filtrationfiltered through a pad of Celite®
  2. customevaporated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane and methanol (95:5)

Sources & evidence

ORD record
ord-918375a2038e4c2396d91fb51244deb4
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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