Benzoyl chloride → 3-(Phenylformamido)butanoic acid

HRID 1421335Notes

Reaction equation

HRID 1421335 reaction equation
[NH2:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>[OH-].[Na+]>[C:8]([NH:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 10932Beta-Aminobutyric Acid

Product 1

HCID 125800473-(Phenylformamido)butanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a cooled solution of 3-aminobutyric acid (13 g) in 2M NaOH (130 ml) is added benzoyl chloride (19.7 g) over the course of two hours. The mixture is allowed to warm to room temperature. Washing with diethyl ether, acidifying the aqueous phase with 20% HCl, extracting with diethyl ether, drying over MgSO4, evaporating the solvent and recrystallizing in either/hexane gives the title compound m.p. 150-152° C. (Compound 1.6, Table 1).

Workup

  1. washWashing with diethyl ether
  2. extractionextracting with diethyl ether
  3. dry with materialdrying over MgSO4
  4. customevaporating the solvent
  5. customrecrystallizing in either/hexane

Sources & evidence

ORD record
ord-455bf8fa641a41c9a857bedaf74b016c
Source dataset
uspto-grants-2000_06
Patent number
US06075051

Reaction notes

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