کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1350405 980441 2007 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Solvent dependency though not solvate formation in the derivative–derivative resolution of N-formylphenylalanine
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Solvent dependency though not solvate formation in the derivative–derivative resolution of N-formylphenylalanine
چکیده انگلیسی

The efficiency of the resolution of N-formylphenylalanine was remarkably improved using (S)-(+)-2-benzylaminobutanol resolving agent in acetone. The efficiency of the resolution strongly depended on the quality of the solvent. Nevertheless, solvate formation did not occur during the process. The nature of the solvent-dependence was studied. The solid-melt binary phase diagram of the diastereomeric salts formed during the resolution by (S)-(+)-2-benzylaminobutanol was measured and discussed. It was recognized that the (S)-(+)-benzylaminobutanol (S)-(+)-N-formylphenylalanine salt exists in two polymorphic modifications.The effect of structurally related chiral and achiral auxiliary reagents in the above resolution was also studied. Thus, (S)-(+)-2-benzylaminobutanol was applied together with an (R)-(+)-1-phenylethylamine auxiliary resolving agent and benzylamine was used as a half-equivalent achiral basic reagent in a Pope–Peachey type resolution of N-formylphenylalanine by (S)-(+)-2-benzylaminobutanol. The results are compared to those obtained by the structurally related (R)-(+)-1-phenylethylamine chiral auxiliary.

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BenzylaminobutanolC11H17NOEe >99.5%[α]D20=+25.2 (c 2, ethanol)Source of chirality: enantiopure resolving agentAbsolute configuration: (S)

N-FormylphenylalanineC10H11NO3Ee >83% by chiral HPLC[α]D20=-62.3 (c 2, ethanol)Source of chirality: optical resolutionAbsolute configuration: (R)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 18, Issue 21, 22 October 2007, Pages 2531–2536
نویسندگان
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