Sodium Hydroxide → HCID 178451662, compound

HRID 340071Notes

Reaction equation

HRID 340071 reaction equation
C(OC([N:8]1[C:16]2[CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C:11]=2[N:10]=[CH:9]1)=O)(C)(C)C.[OH-].[Na+]>CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:20]([O:19][C:17]([N:13]1[CH2:14][CH2:15][C:16]2[NH:8][CH:9]=[N:10][C:11]=2[CH2:12]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71238558HCID 71238558, compound

Product 1

HCID 178451662HCID 178451662, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 6,7-dihydro-4H-imidazo[4,5-c]pyridine-1,5-dicarboxylic acid di-tert-butyl ester (Preparation 19, 26.8 g, 82.9 mmol) in methanol (210 mL) was added 1M sodium hydroxide aqueous solution (170 mL, 170 mmol). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with 10% citric acid aqueous solution (250 mL), basified to pH8 and extracted with DCM (2×500 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the title compound as a brown foam (18.5 g) in a 97% yield.

Workup

  1. extractionextracted with DCM (2×500 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68391fe84f8f4e679029f12663fb5c33
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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