Ethyl Acetate → HCID 86725285, compound

HRID 1478889Notes

Reaction equation

HRID 1478889 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][N+:10]=1[O-])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].CCOC(C)=O>C1COCC1.[Zn]>[C:1]([O:5][C:6]([N:8]([CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:9]1[N:10]=[CH:11][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 86725284HCID 86725284, compound

Product 1

HCID 86725285HCID 86725285, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 2-(tert-butoxycarbonyl(2-(tert-butoxycarbonylamino)ethyl)amino)-5-(carboxymethyl)pyridine 1-oxide (0.78 g) in a mixture of THF (10 mL) and sat. NH4Cl (10 mL) was added Zinc dust (0.65 g). The reaction mixture was stirred at room temperature for overnight. EtOAc was then added and washed with water. The organic phase was dried and concentrated to afford the desired product (0.5 g).

Workup

  1. washwashed with water
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-79ff4c3e4d0c40b3b5eed0457cda02f9
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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