Hydrochloric Acid → HCID 90370333, compound

HRID 2176014Notes

Reaction equation

HRID 2176014 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][CH2:8][C:9]([N:11]([CH3:32])[CH2:12][CH2:13][N:14]([CH2:20][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][N:31]=1)[C:24]([O:26]CC)=[O:25])[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CO.Cl>O.C1COCC1>[C:1]([O:5][C:6](=[O:33])[CH2:7][CH2:8][C:9]([N:11]([CH3:32])[CH2:12][CH2:13][N:14]([CH2:20][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][N:31]=1)[C:24]([OH:26])=[O:25])[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 90370129HCID 90370129, compound

Product 1

HCID 90370333HCID 90370333, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.9 g of ethyl 2-{[{2-[(4-tert-butoxy-4-oxobutanoyl)(methyl)amino]ethyl}(pentan-3-yl)amino]methyl}isonicotinate, 8.2 mL of a 1.0 M aqueous sodium hydroxide solution, 8.0 mL of methanol, and 16 mL of THF was stirred overnight at room temperature. The mixture was neutralized using 1.0 M hydrochloric acid, water was added thereto, followed by extraction with chloroform-methanol. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure, thereby obtaining 1.5 g of 2-{[{2-[(4-tert-butoxy-4-oxobutanoyl)(methyl)amino]ethyl}(pentan-3-yl)amino]methyl}isonicotinic acid.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with chloroform-methanol
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e3bb1a64d9b14153ad43c46d3113dae4
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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