Hydrochloric Acid → HCID 22326861, compound

HRID 495485Notes

Reaction equation

HRID 495485 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[NH2:19])C.[OH-].[Na+].Cl>C1COCC1>[NH2:19][C:10]1[CH:11]=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:9]=1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:20])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 697384545-(2-amino-4,5-dimethoxy-phenyl)-pentanoic Acid Ethyl Ester

Product 1

HCID 22326861HCID 22326861, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-amino-4,5-dimethoxy-phenyl)-pentanoic acid ethyl ester (Example 122, Step B) (0.1 g, 0.35 mmol) in THF (3 mL) was added NaOH (2 M, aqueous) (3 mL) and the mixture was stirred vigorously at RT for 12 h. The reaction was neutralized by the slow addition of HCl (2 N, aqueous) followed by removal of the THF under reduced pressure. The aqueous mixture was extracted with CH2Cl2 (3×10 mL) and the organic layers were combined, washed with brine, dried with MgSO4, and filtered. Concentration under reduced pressure afforded the title compound as a brown solid that was carried on without purification.

Workup

  1. customfollowed by removal of the THF under reduced pressure
  2. extractionThe aqueous mixture was extracted with CH2Cl2 (3×10 mL)
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-4321f4899e4e493c95c50860eb2ebedf
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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