Sodium Hydroxide → HCID 86725284, compound

HRID 1478888Notes

Reaction equation

HRID 1478888 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]C)=[O:17])=[CH:11][N+:10]=1[O-:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1.Cl>[C:1]([O:5][C:6]([N:8]([CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][N+:10]=1[O-:20])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86725283HCID 86725283, compound

Product 1

HCID 86725284HCID 86725284, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 2-(tert-butoxycarbonyl(2-(tert-butoxycarbonylamino)ethyl)amino)-5-(2-methoxy-2-oxoethyl)pyridine 1-oxide from step 4 in a mixture of MeOH/THF (20 mL, 1:1) was added 1 N NaOH. The reaction mixture was stirred at room temperature overnight. IN HCl was added to acidify the solution to pH 4. The aqueous phase was extracted with EtOAc (3×). The combined organic phases were dried and concentrated. The residue was then purified by reverse phase chromatography to afford the product (1.4 g).

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (3×)
  2. customThe combined organic phases were dried
  3. concentrationconcentrated
  4. customThe residue was then purified by reverse phase chromatography

Sources & evidence

ORD record
ord-2944d97f7a914394a86bf79b17ee79a7
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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