4-(Benzoylamino)butyric acid synthesis

8synthesis methods

Product Name:4-(Benzoylamino)butyric acid
CAS Number:35340-63-7
Molecular formula:C11H13NO3
Molecular Weight:207.23

98-88-4 Synthesis

98-88-4
577 suppliers
$10.00/5g

56-12-2 Synthesis

56-12-2
843 suppliers
$5.00/100mg

35340-63-7
32 suppliers
$44.00/100mg

Yield:35340-63-7 94%

Reaction Conditions:

with sodium hydroxide in water at 0 - 20;Inert atmosphere;

Steps:

4-Benzamido butanoic acid

γ-Aminobutyric acid (0.30 g, 2.91 mmol) and NaOH (0.21 g, 5.24 mmol) were dissolved in H₂0 (6 mL). The resulting solution was cooled to 0 °C and to this was added dropwise benzoyl chloride (0.31 mL, 2.63 mL). The mixture was stirred for two hours at 0 °C and then at room temperature overnight. The resulting solution was acidified with cone. HC1 to pH 2, extracted with ethyl acetate (3 x 30mL), dried over Na₂S0₄, and concentrated in vacuo. The residue was taken up in minimal ethanol followed by the addition of water until a cloudy solution was formed. The solution was concentrated to yield a white solid which was triturated with hexane and filtered to yield a crystalline solid (1.41 g, 94%); mp 88-89 °C. ^lR NMR (500 MHz, methanol-^) 5 7.79-7.87 (m, J=0.95, 8.51 Hz, 1H), 7.50-7.56 (m, 2H), 7.43-7.50 (m, 3H), 3.45 (t, j=6.94 Hz, 2H), 2.41 (t, J=7.25 Hz, 2H), 1.94 (quin, J=7.17 Hz, 2H). ¹³C MR (126 MHz, methanol-^) δ 182.1, 137.5, 136.9, 129.4, 128.3, 42.5, 36.1, 24.8, 21.3.

References:

WO2014/18913,2014,A2 Location in patent:Page/Page column 46