Hydrochloric Acid → HCID 68814467, compound

HRID 732411Notes

Reaction equation

HRID 732411 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[N:8]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=1)=[O:4].Cl>C1COCC1.[OH-].[Li+]>[CH3:20][CH2:19][O:18][C:16]([C:7]1[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[C:9]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[N:8]=1)=[O:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68817414HCID 68817414, compound

Product 1

HCID 68814467HCID 68814467, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (S)-6-sec-butylaminopyridine-2,4-dicarboxylic acid 2-ethyl ester 4-methyl ester (990 mg, 3.5 mmol) in THF (35 mL) and dropwise add 1 N lithium hydroxide solution (3.5 mL). Stir at room temperature for 2 h and acidify the mixture to about pH=4 by 5 N HCl and concentrate to near dryness. Dilute with ethyl acetate (20 mL) and wash the organic layer with saturated sodium chloride solution, dry (magnesium sulfate) and concentrate to give a 2:1 ratio of crude title compound to starting material which is used in the next step without further purification.

Workup

  1. concentrationconcentrate to near dryness
  2. additionDilute with ethyl acetate (20 mL)
  3. washwash the organic layer with saturated sodium chloride solution
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-65897ec1795241aeb35cba404369155f
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…