Hydrochloric Acid → HCID 90281966, compound

HRID 1497518Notes

Reaction equation

HRID 1497518 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:20][C:21]1[N:26]=[C:25]([C:27]([O:29]CC)=[O:28])[CH:24]=[CH:23][CH:22]=1)[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]([CH2:20][C:21]1[N:26]=[C:25]([C:27]([OH:29])=[O:28])[CH:24]=[CH:23][CH:22]=1)[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90282120HCID 90282120, compound

Product 1

HCID 90281966HCID 90281966, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-({[(benzyloxy)carbonyl](2-tert-butoxy-2-oxoethyl)amino}methyl)pyridine-2-carboxylate (3.26 g) in tetrahydrofuran (10.0 mL) were added a 1 M aqueous sodium hydroxide solution (8.00 mL), followed by stirring at room temperature overnight. To the reaction mixture was added 1 M hydrochloric acid (8.00 mL), followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 6-({[(benzyloxy)carbonyl](2-tert-butoxy-2-oxoethyl)amino}methyl)pyridine-2-carboxylic acid (2.08 g).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-03ec302418364070963e03c0fea804c3
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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