HCID 66789405, compound → HCID 66789429, compound

HRID 1660796Notes

Reaction equation

HRID 1660796 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:7]([N+:19]([O-])=O)[CH:6]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])=[C:7]([NH2:19])[CH:6]=1)[CH3:2]

Participants

4

Reactant 1

HCID 66789405HCID 66789405, compound

Product 1

HCID 66789429HCID 66789429, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Tert-butoxycarbonylamino-3-nitro-benzoic acid ethyl ester (3.5 g, 11.3 mmol) was dissolved in ethanol (300 mL) and 10% palladium on carbon was added (0.45 g, 0.42 mmol). The mixture was evacuated and filled with hydrogen, then stirred at room temperature for 1 hour. The catalyst was filtered, washing with ethanol, and the solvent was evaporated. The crude 3-amino-4-tert-butoxycarbonylamino-benzoic acid ethyl ester thus obtained [3.1 g, 95%, MS (ISP): m/e=279.3 (M−H)] was used as such in the following reaction.

Workup

  1. customThe mixture was evacuated
  2. additionfilled with hydrogen
  3. filtrationThe catalyst was filtered
  4. washwashing with ethanol
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c37bc2e11ab74d3da630ce81b3b338ce
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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