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Efficient synthesis of (Z)- and (E)-methyl 2-(methoxyimino)-2-phenylacetate |
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| Authors: | Yong-Jin Wu Stella Huang Qi Gao David R. Langley |
| Affiliation: | a Department of Neuroscience Chemistry, Research and Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, CT 06492, USA b Analytical Research and Development, Research and Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, CT 06492, USA c Bioanalytical and Discovery Analytical Sciences, Research and Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, CT 06492, USA d Analytical Research and Development, Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, NJ 08901, USA e Department of Computer-Aided Drug Design, Research and Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, CT 06492, USA |
| Abstract: | Direct oximation of 2-oxo-2-phenylacetate (3) gave the (Z)-methyl 2-(methoxyimino)-2-phenylacetate (1) in 71% yield, while the E oxime 2 was prepared from 3 in 65% yield via oxime isomerization of 2-(methoxyimino)-2-phenylacetic acid (5). Computational studies suggest that the isomerization of 5 is thermodynamically driven, while the direct oximation of ketoester 3 is kinetically controlled. |
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