Hydrochloric Acid → HCID 67494799, compound

HRID 2047003Notes

Reaction equation

HRID 2047003 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][CH2:6]1)=[O:4].O.[OH-].[Na+].Cl>C1COCC1>[C:14]([O:13][C:11]([N:9]1[CH:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:10]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67494598HCID 67494598, compound

Product 1

HCID 67494799HCID 67494799, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Piperidine-1,2,5-tricarboxylic acid 1,2-di-tert-butyl ester 5-methyl ester (36.7 mmol, 12.6 g) was dissolved in 180 mL of 2:1 THF:H2O. To this solution was added 2N sodium hydroxide solution (52 mL) and the reaction mixture was stirred for 16 h at room temperature. The reaction mixture is acidified to pH=3 with 1N HCl(aq) and extracted with dichloromethane (3×100 mL). The combined organics are then dried over Na2SO4 and the solvent removed in vacuo to yield the title compound (12.0 g, 100% yield).

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. dry with materialThe combined organics are then dried over Na2SO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b84f774cfc234900b26eeba16ef2f633
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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