Ammonium formate → HCID 67352508, compound

HRID 1676032Notes

Reaction equation

HRID 1676032 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[NH:6][C@@H:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([O-])=O.C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:1][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[NH:6][C@@H:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 67352530HCID 67352530, compound

Product 1

HCID 67352508HCID 67352508, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl (3R)-3-(2-nitroanilino)-3-phenylpropanoate (100 mg, 292 μmol) in a mixture of ethanol and water (4 mL, 3:1), was added palladium on carbon (20 mg, 10% w/w Pd) and ammonium formate (191 mg, 3.03 mmol). The suspension was heated to reflux for 10 minutes, and was then cooled to room temperature, filtered through a pad of Celite®, and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (98:2) to afford the title compound, 1H NMR: (CD3OD) 7.41 (d, J=7.3, 1H), 7.33-7.31 (m, 2H), 7.25-7.21 (m, 1H), 6.75-6.73 (m, 1H), 6.72-6.52 (m, 2H), 6.47-6.45 (m, 1H), 4.82 (obs., 1H), 2.87 (dd, J=14.6, 7.7, 1H), 2.74 (dd, J=14.6, 6.2, 1H), 1.41 (s, 9H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 10 minutes
  3. filtrationfiltered through a pad of Celite®
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane and methanol (98:2)

Sources & evidence

ORD record
ord-f7cd0abcfdef4a8fad67e5e9f17e4b41
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

Loading…