Hydrochloric Acid → HCID 68814467, compound

HRID 1436555Notes

Reaction equation

HRID 1436555 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-2c1cb5407dbe4ff7885b228e95b2b40d
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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