H-GAMMA-ABU-OBZL P-TOSYLATE synthesis
- Product Name:H-GAMMA-ABU-OBZL P-TOSYLATE
- CAS Number:26727-22-0
- Molecular formula:C18H23NO5S
- Molecular Weight:365.44
104-15-4
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100-51-6
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$5.00/100g
56-12-2
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26727-22-0
64 suppliers
$23.30/5G
Yield:26727-22-0 99%
Reaction Conditions:
in toluene; for 5 h;Reflux;
Steps:
Compound 2.
A suspension of γ-aminobutanoic acid (GABA) 1 (3.50 g, 0.034 mol), benzyl alcohol (7.30 g, 7 mL,0.068 mmol) and p-toluenesulfonic acid monohydrate (PTSA) (7.10 g, 0.037 mol) in PhMe (200 mL) was heated toreflux for 5 h with azeotropic removal of water. The reaction mixture was concentrated to a one third of the volumeand the product precipitated by addition of Et2O (100 mL). The precipitate was filtered, dissolved in CH3OH (60 mL)and again precipitated by addition of Et2O (100 ml), giving after filtration and drying the benzyl ester 2 (12.30 g,99%) as white crystals. M.p. 106.2-106.7 C (Et2O); IR(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; MS(ESI): Calcd for C11H16NO2 (M+H)+: 194.1181, found: 194.1167.
References:
Kop, Tatjana J.;?or?evi?, Jelena;Bjelakovi?, Mira S.;Mili?, Dragana R. [Tetrahedron,2017,vol. 73,# 50,p. 7073 - 7078]
100-51-6
1431 suppliers
$5.00/100g
56-12-2
893 suppliers
$5.00/100mg
26727-22-0
64 suppliers
$23.30/5G