Benzoyl chloride → 3-(Phenylformamido)butanoic acid

HRID 355433Notes

Reaction equation

HRID 355433 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 of the aqueous phase with 20% HCI, extraction with diethyl ether, drying over MgSO4, evaporation of the solvent and recrystallization in ether/hexane gives the title compound m.p. 150°-152° C. (compound 1.16, Table 1).

Workup

  1. washWashing with diethyl ether, acidifying of the aqueous phase with 20% HCI, extraction with diethyl ether
  2. dry with materialdrying over MgSO4, evaporation of the solvent and recrystallization in ether/hexane

Sources & evidence

ORD record
ord-537ccc3806ee401eacc4b26539a26b88
Source dataset
uspto-grants-1998_11
Patent number
US05830919

Reaction notes

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