Hydrochloric Acid → 4-{[(Tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid

HRID 1660916Notes

Reaction equation

HRID 1660916 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[N:6][CH:5]=1.[OH-].[Na+].Cl>O1CCOCC1>[C:14]([O:13][C:11]([NH:10][C:9]1[C:4]([C:3]([OH:18])=[O:2])=[CH:5][N:6]=[CH:7][CH:8]=1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23438729Methyl 4-((tert-butoxycarbonyl)amino)nicotinate

Product 1

HCID 221726234-{[(Tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-tert-butoxycarbonylamino-nicotinic acid methyl ester (6.02 g, 23.86 mmol) in dioxane (100 mL) was added aq. sodium hydroxide (0.970 N solution, 28.05 mL, 27.20 mmol). The solution was heated to 60° C. for 1 hr then cooled. Aqueous hydrochloric acid (1.03 μM solution, 26.99 mL, 27.20 mmol) was added and the mixture was extracted with chloroform (5×100 mL). The extracts were dried (MgSO4), filtered, and evaporated to give 4-tert-Butoxycarbonylamino-nicotinic acid, a cream solid (4.70 g, 83% yield).

Workup

  1. temperaturethen cooled
  2. extractionthe mixture was extracted with chloroform (5×100 mL)
  3. dry with materialThe extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-225263d9d41a4bfc858bdb645bd5332e
Source dataset
uspto-grants-2011_10
Patent number
US08030318B2

Reaction notes

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