Ammonium formate → Methyl 2-amino-5-((((tert-butoxy)carbonyl)amino)methyl)benzoate

HRID 884502Notes

Reaction equation

HRID 884502 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:20]([O-])=O)=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:20][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 19698365Methyl 5-tert-butoxycarbonylaminomethyl-2-nitrobenzoate

Product 1

HCID 60103040Methyl 2-amino-5-((((tert-butoxy)carbonyl)amino)methyl)benzoateYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.273 g of methyl 5-{[(tert-butoxycarbonyl)amino]methyl}-2-nitrobenzoate, 0.166 g of ammonium formate and 0.094 g of Pd/C (10%) in 10 ml of EtOH purged beforehand with nitrogen is irradiated under a microwave field at 120° C. for 5 min. The mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an AcOEt/heptane mixture, (5/95, v/v) as far as (30/70, v/v), to give 0.2 g of the expected product.

Workup

  1. customis irradiated under a microwave field at 120° C. for 5 min
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-9d2658e95c924ce7af43d372f19f102e
Source dataset
uspto-grants-2012_08
Patent number
US08242126B2

Reaction notes

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