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[ Last edited by wjh686 on 2008-3-25 at 19:00 ]

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Tetrahedron Lett.; EN; 42; 3; 2001; 509 - 512.
J. Chem. Soc. Dalton Trans.; EN; 6; 1990; 1867-1872.
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1-propanesulfonic acid (Compound GN); L-Phenylglycine amide hydrochloride (1.0 g, 6.7 mmol) was treated with a solution of K2CO3 (20 mL). The resultant mixture was extracted with EtOAc (3.x.20 mL). The organic extracts were separated, combined, dried over Na2SO4. The solid material was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure. To a solution of L-Phenylglycine amide (670 mg, 5.9 mmol) in tetrahydrofuran (10 mL) and 1,4-dioxane (4 mL) was added 1,3-propanesultone (674 mg, 5.6 mmol). The solution stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration and washed with acetone (2.x.20 mL). The solid was dissolved in 50percent water/EtOH mL). Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure. The solid was suspended in acetone (50 mL), filtered and dried in the vacuum oven (50.deg. C.), affording the title compound (743 mg, 50percent).


Publ.: US2006/223855 A1 (2006/10/05), Appl.: US2005-316693 (2005/12/21)

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