Ethyl 2-amino-α-(E-methoxyimino)-4-thiazoleacetate hydrobromide

Gavara, Laurent; Parmentier, C.; Evrard, G.; Durant, F.

doi:10.1107/s0567740881004810

Cited by 6 publications

(9 citation statements)

References 2 publications

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“…For general background, see: Johnson (1999); Lynch et al (1999); Powers et al (2001); Toplak et al (2003). For related structures, see: Laurent et al (1981); Yoshida et al (1989). Mo K radiation = 0.21 mm À1 T = 223 (2) K 0.80 Â 0.80 Â 0.57 mm…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound is a very important intermediate of ceftazidime, which is among the most important cephalosporin antibiotics (Powers et al, 2001). Crystal structures of some cephalosporin intermediates which contain a 2-aminothiazole group have been reported (Yoshida et al, 1989;Laurent et al, 1981). The title compound can give a reactive intermediate by reaction with diethylenetriamine-N,N,N′,N′′,N′′-pentaacetic acid (DTPA), further, which can be used to prepare a protein-chelator conjugate (Johnson, 1999).…”

Section: Data Collectionmentioning

confidence: 99%

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(Z)-2-(2-Aminothiazol-3-ium-4-yl)-2-[2-(tert-butoxycarbonyl)isopropoxyimino]acetate monohydrate

Cheng

2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 223 K; mean (C-C) = 0.002 Å; disorder in main residue; R factor = 0.041; wR factor = 0.091; data-to-parameter ratio = 12.1.In the title compound, C 13 H 19 N 3 O 5 SÁH 2 O, the amino group is coplanar with the thiazole ring. The dihedral angle between the thiazole ring and the adjacent carboxylate group is 86.9 (1) . The tert-butyl group is disordered over two positions, with occupancies of 0.63 (4) and 0.37 (4). O-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds link the molecules into a twodimensional network parallel to the (001) plane. The thiazole rings of inversion-related molecules are stacked with their centroids separated by a distance of 3.5387 (10) Å , indicating interactions.

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Section: Related Literaturementioning

confidence: 99%

Section: Data Collectionmentioning

confidence: 99%

(Z)-2-(2-Aminothiazol-3-ium-4-yl)-2-[2-(tert-butoxycarbonyl)isopropoxyimino]acetate monohydrate

Cheng

2007

Acta Cryst E

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“…For general background, see: Quintiliani (1996); Lynch et al (1999); Toplak et al (2003). For related structures, see: Laurent et al (1981); Yoshida et al (1989). For related literature, see: Allen (2002).…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound is an important intermediate of cefixime, which was the first oral third-generation cephalosporin available in Japan, The United States, Europe and other regions (Quintiliani, 1996). Crystal structures of some cephalosporin intermediates which contain a 2-aminothiazole group have been reported (Yoshida et al, 1989;Laurent et al, 1981).…”

Section: Supporting Informationmentioning

confidence: 99%

(Z)-2-(2-Aminothiazol-1-ium-4-yl)-2-(tert-butoxycarbonylmethoxyimino)acetate monohydrate

Cheng

2007

Acta Cryst E

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In the title compound, C11H15N3O5S·H2O, the amino group is coplanar with the thiazole ring. The dihedral angle between the thiazole ring and the adjacent carboxylate group is 74.19 (4)°. O—H...O and N—H...O hydrogen bonds link the molecules into two‐dimensional networks parallel to the (100) plane, and π–π interactions exist between the thiazole rings of inversion‐related molecules, with a centroid–centroid separation of 3.5965 (6) Å.

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“…For the crystal structures of related compounds, see: Laurent et al (1981). For details of the biological activities of strobilurin compounds, see: Bartlett et al (2002); Sauter et al (1999).…”

Section: Related Literaturementioning

confidence: 99%