26727-22-0

基本信息
4-氨基丁酸芐酯對甲基苯磺酸鹽
4-氨基丁酸芐酯4-甲基苯磺酸鹽
GAMMA-氨基丁酸芐酯對甲苯磺酸鹽
BENZYL 4-AMINOBUTANOATE,4-METHYLBENZENESULFONIC ACID
H-GABA-OBzl·TosOH
H-g-Abu-OBzl·TosOH
H-γ-Abu-OBzl·TosOH
H-ABU(4)-OBZL TOS-OH
Hγ-Abu-OBzl·p-tosylate
H-GAMMA-ABU-OBZL TOS-OH
H-GABA-OBzl · p-tosylate
gamma-Abu-OBzl p-tosylate
H-g-Abu-OBzl · p-tosylate
制備方法

104-15-4

100-51-6

56-12-2

26727-22-0
在甲苯(200 mL)中,將γ-氨基丁酸(GABA)(3.50 g,0.034 mol)、苯甲醇(7.30 g,7 mL,0.068 mol)和對甲苯磺酸一水合物(PTSA)(7.10 g,0.037 mol)的懸浮液加熱至回流5小時,通過共沸蒸餾除去生成的水。反應(yīng)完成后,將混合物濃縮至原體積的三分之一,隨后加入乙醚(100 mL)使產(chǎn)物沉淀。過濾收集沉淀,將其溶解于甲醇(60 mL)中,再次加入乙醚(100 mL)進行重沉淀。過濾后,干燥得到白色晶體狀的4-氨基丁酸芐酯4-甲基苯磺酸鹽(12.30 g,收率99%)。產(chǎn)物的熔點為106.2-106.7°C(乙醚中測定);紅外光譜(ATR):3100, 3039, 2942, 1732, 1642, 1532, 1188, 1125 cm^-1;^1H NMR(200 MHz,CD3OD):δ=7.71(d,J=8.0 Hz,2H,HPTSA),7.37-7.30(m,5H,HCAr),7.20(d,J=8.4 Hz,2H,HPTSA),5.11(s,2H,H2CBn),2.95(t,J=7.5 Hz,2H,H2C(4)GABA),2.47(t,J=7.3 Hz,2H,H2C(2)GABA),2.33(s,3H,H3CPTSA),1.92(quint,J=7.4 Hz,2H,H2C(3)GABA)ppm;^13C NMR(50 MHz,CD3OD):δ=173.83(CO2Bn),143.35, 141.82, 137.43, 129.91, 129.59, 129.30, 126.91(CAr),67.44(CH2Bn),40.00(CH2(4)GABA),31.59(CH2(2)GABA),23.65(CH2(3)GABA),21.30(CH3PTSA)ppm;質(zhì)譜(ESI):C11H16NO2([M+H]+)的計算值:194.1181,實測值:194.1167。
參考文獻:
[1] Tetrahedron, 2017, vol. 73, # 50, p. 7073 - 7078
[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 11, p. 2327 - 2337
[3] RSC Advances, 2015, vol. 5, # 81, p. 66339 - 66354
[4] Patent: WO2014/59158, 2014, A1. Location in patent: Page/Page column 38-39
[5] Tetrahedron Letters, 2015, vol. 56, # 48, p. 6803 - 6806