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Separation of ( R )‐ and ( S )‐ tert ‐butyl 2‐ tert ‐butyl‐4‐methoxy‐2,5‐dihydro‐1,3‐imidazole‐1‐carboxylate (building block for amino acid synthesis) by preparative high performance liquid chromatography on a polysaccharide stationary phase
Author(s) -
Hoffmann Matthias,
Blank Stefan,
Seebach Dieter,
Küsters Ernst,
Schmid Emil
Publication year - 1998
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1998)10:3<217::aid-chir3>3.0.co;2-6
Subject(s) - chemistry , enantiomer , high performance liquid chromatography , silica gel , imidazole , chromatography , chirality (physics) , chiral column chromatography , amylose , phase (matter) , hexane , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , starch , nambu–jona lasinio model , quark
The preparative separation of the enantiomers of the title compound, a versatile chiral building block for the synthesis of unnatural amino acid esters, by high performance liquid chromatography on a chiral stationary phase (CSP), is reported for the first time. The CSP consists of amylose‐(3,5‐dimethylphenyl‐carbamate), which has been coated onto the surface of macroporous aminopropyl‐functionalized silica gel. The effect of mobile phase composition and the amount of amylose derivative on the silica gel has been thoroughly investigated. Using 2‐propanol as organic modifier in hexane as mobile phase, on a semi‐preparative column (200 mm × 40 mm ID, containing 192 g of stationary phase) about 200 mg of the racemate was separated per injection. Running the equipment under automatic conditions with repetitive injection mode allowed for the separation of 30 g per day. Both enantiomers were obtained with enantiopurities >99.75:0.25. Chirality 10:217 – 222, 1998 . © 1998 Wiley‐Liss, Inc.