Reactions of (S)-(4-nitrophenyl)[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl methanesulfonate with alkali metal halides and lithium hydroxide. Synthesis of [(2R,3R)-3-(4-nitrophenyl)aziridin-2-yl]-methanol

Madesclaire, M.; Coudert, Pascal; Leal, F.; Tarrit, Sébastien; Zaitseva, Yu. V.; Zaitsev, V. P.

doi:10.1007/s10593-013-1350-x

Cited by 3 publications

(4 citation statements)

References 9 publications

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“…For related structures, see: Bach et al (2001); Tsui et al (2013). For detailed of the synthesis, see: Madesclaire et al (2013).…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound was obtained as a by-product from the reaction of 4-[hydroxy(4-nitrophenyl)methyl]-1,3oxazolidin-2-one and benzenesulfonyl chloride with pyridine in chloroform. The synthesis process is described by Madesclaire et al (2013). After isolation and purification by column chromatography, crystals suitable for X-ray analysis were obtained by slow evaporation from a mixture of ethyl acetate-cyclohexane (1:1 vol.)…”

Section: S2 Experimentalmentioning

confidence: 99%

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(4S)-4-[(R)-Chloro(4-nitrophenyl)methyl]-1,3-oxazolidin-2-one

Gaumet¹,

Denis²,

Madesclaire³

et al. 2013

Acta Cryst E

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In the title compound, C10H9ClN2O4, the oxazolidinone ring adopts a near-planar conformation, with mean and maximum deviations of 0.0204 (8) and 0.0328 (8) Å, respectively. The nitro group is twisted slightly from the plane of the benzene ring, making a dihedral angle of 6.79 (3)°. The dihedral angle between the mean oxazolidinone plane and the benzene ring is 56.21 (3)°. In the crystal, N—H⋯O hydrogen bonds and N—O⋯π interactions [O⋯centroid distances = 3.478 (1) and 3.238 (1) Å] dominate the packing, forming infinite zigzag chains along the b-axis direction. Neighbouring chains are linked together through C—H⋯O and C—H⋯Cl interactions. The absolute configuration of the two stereogenic centres was determined using the anomalous dispersion of the Cl atom.

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“…For related structures, see: Bach et al (2001); Tsui et al (2013). For detailed of the synthesis, see: Madesclaire et al (2013).…”

Section: Related Literaturementioning

confidence: 99%

Section: S2 Experimentalmentioning

confidence: 99%

(4S)-4-[(R)-Chloro(4-nitrophenyl)methyl]-1,3-oxazolidin-2-one

Gaumet¹,

Denis²,

Madesclaire³

et al. 2013

Acta Cryst E

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“…(2R,3R)-3-(4-Nitrophenyl)aziridin-2-yl]methanol was synthesized from (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3propandiol by the four-step method developped by Madesclaire et al (2013). Plate and colourless crystals of the title coumpund were obtained by slow evaporation in air of a 1:10 (v/v) methanol-ethyl acetate solution.…”

Section: S2 Experimentalmentioning

confidence: 99%

“…For related structures, see: Zhu et al (2006). For details of the synthesis, see: Madesclaire et al (2013). For determination of the absolute configuration, see: Hooft et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

[(2R,3R)-3-(4-Nitrophenyl)aziridin-2-yl]methanol monohydrate

Gaumet¹,

Denis²,

Leal³

et al. 2013

Acta Cryst E

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The title monohydrate, C9H10N2O3·H2O, contains an aziridine ring including two contiguous stereocenters, both of which exhibit an R configuration. The methylhydroxy and nitrophenyl groups are cis-disposed about the aziridine ring. The mean plane of the benzene ring is tilted to the aziridine ring by 66.65 (8)°. The nitro group is nearly coplanar with the benzene ring [dihedral angle = 2.5 (2)°]. In the crystal, the components are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, generating supramolecular layers parallel to (001).

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