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Resolution of optical isomers of 4-amino-p-chlorobutyric acid lactam by co-crystallization

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Abstract

4-Amino-p-chlorobutyric acid lactam crystallizes as racemic crystals in the monoclinic space groupP21/n, witha=5.006(2),b=6.783(2),c=27.652(2) Å, β=92.25(1)°,Z=4,R=0.035 for 1618 unique reflections. As both enantiomers are present in a single crystal it is not possible to effect enantiomeric separation by crystal growth inhibition. This lactam may, however, be co-crystallized with (2R,3R)-(+)-tartaric acid forming a 2:1 complex in which only the (R) enantiomer is present. The complex crystallizes in the monoclinic space groupP21 witha=10.074(2),b=10.132(6),c=12.238(6) Å, β=99.13(2)°,Z=2,R=0.036 for 2291 unique reflections. Complex formation is effected by hydrogen bonding but enantioselectivity does not involve the chiral center of the title compound directly.

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Caira, M.R., Nassimbeni, L.R., Scott, J.L. et al. Resolution of optical isomers of 4-amino-p-chlorobutyric acid lactam by co-crystallization. J Chem Crystallogr 26, 117–122 (1996). https://doi.org/10.1007/BF01669727

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  • DOI: https://doi.org/10.1007/BF01669727

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