Ethanol → HCID 71186559, compound

HRID 712857Notes

Reaction equation

HRID 712857 reaction equation
C([N:8]1[CH2:11][CH2:10][CH:9]1[C:12]([NH:14][C@H:15]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)[CH3:16])=[O:13])C1C=CC=CC=1.CCO.C([O-])=O.[NH4+]>[Pd]>[NH:8]1[CH2:11][CH2:10][CH:9]1[C:12]([NH:14][C@H:15]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)[CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formate2×HCID 71186307HCID 71186307, compound

Product 1

HCID 71186559HCID 71186559, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of methyl 4-((1S)-1-(1-benzylazetidine-2-carboxamido)ethyl)benzoate (D76) (98 mg, 0.278 mmol in EtOH (20 ml) Pd/C 10% (90 mg, 0.083 mmol) and ammonium formate (52 mg, 0.83 mmol) were added and the heterogeneous solution was left stirring at RT for 20 hrs. Further addition of Pd/C 10% (90 mg, 0.083 mmol) and ammonium formate (52 mg, 0.83 mmol) was done and the resulting mixture was stirred at RT for 5 hrs. Catalyst was filtered off and the solvent evaporated to afford the title compound (D109) (60 mg).

Workup

  1. waitthe heterogeneous solution was left
  2. stirringthe resulting mixture was stirred at RT for 5 hrs
  3. filtrationCatalyst was filtered off
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-34d8cbf8200848a1950b648946eba19f
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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