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86499-52-7

(S)-3-AMino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic Acid Ethyl Ester synthesis

5synthesis methods
-

Yield:86499-52-7 26.5%

Reaction Conditions:

with tartaric acid in ethanol at 0 - 20; for 120 h;

Steps:

4.A(6)

A solution of Part A(5) compound (14.8 g, 56.4 moles) and L-tartaric acid (8.50 g) in hot absolute ethanol (118 ml) was kept overnight at 0°, at room temperature for 3 days and then at 0° for another 2 days. The solid that formed was recrystallized from absolute ethanol (118 ml) two more times until a consistent specific rotation was obtained. The precipitates (6.319 g) from the second recrystallization was then suspended in EtOAc (100 ml), treated with 10% NH4OH (12 ml) and stirred for 5 minutes. The organic phase was separated, washed with 10% NH4OH (10 ml) and brine (15 ml), dried (anhydrous Na2SO4), filtered, evaporated to dryness and dried in vacuo to give title compound as a white solid (3.927 g, m.pt. 105-107°, 26.5%) with consistent 1H-NMR and 13C-NMR spectral data. [00187] [a]D=-277° (c 0.99, EtOH). TLC: Rf 0.45 (Silica gel; CH2Cl2:CH3OH-9:1; UV).

References:

US6777550,2004,B1 Location in patent:Page column 29