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【结 构 式】

【分子编号】11299

【品名】2-hydroxyethyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate

【CA登记号】

【 分 子 式 】C11H11NO6S

【 分 子 量 】285.27748

【元素组成】C 46.31% H 3.89% N 4.91% O 33.65% S 11.24%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

This compound can be prepared by two similar ways: 1) The monoacylation of ethylene glycol (I) with chloroacetyl chloride (II) and triethylamine gives 2-hydroxyethyl chloroacetate (III), which is condensed with saccharine (IV) by means of NaOH in ethylene glycol yielding 2-hydroxyethyl 3-oxo-1,2-benzisothiazoline-2-acetate 1,1-dioxide (V). Isomerization of (V) by means of potassium tert-butoxide in DMSO affords2-hydroxyethyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (VI), which is methylated with NaOH and methyl iodide in aqueous ethanol giving the corresponding N-methyl derivative (VII). Hydrolysis of (VII) with NaOH in ethanol - water yields the corresponding free acid (VIII), which is acylated with cinnamoyl chloride (IX) by means of triethylamine in dichloromethane to afford the biscinnamoyl derivative (X). Finally, this compound is treated with 2-aminopyridine (XI) in dichloromethane. 2) The preceding sequence can also be carried out with cyclohexanol (XII) instead of ethylene glycol (I), then producing compounds (XIII), (XIV), (XV) and (XVI), which by hydrolysis affords the free acid (VIII).

1 Bruzzese, T.; Dell'Acqua, E.; Ottonni, F.; Van den Heuvel, H.H. (SPA (Societa Prodotti Antibiotici)); Process for preparing benzothiazine compds. EP 0146102 .
2 Prous, J.; Castaner, J.; CINNOXICAM. Drugs Fut 1990, 15, 2, 119.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(II) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(III) 11297 2-hydroxyethyl 2-chloroacetate C4H7ClO3 详情 详情
(IV) 11298 1H-1,2-Benzisothiazole-1,1,3(2H)-trione; Saccharin 81-07-2 C7H5NO3S 详情 详情
(V) 11299 2-hydroxyethyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate C11H11NO6S 详情 详情
(VI) 11300 2-hydroxyethyl 4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C11H11NO6S 详情 详情
(VII) 11301 2-hydroxyethyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C12H13NO6S 详情 详情
(VIII) 11302 4-Hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylic acid C10H9NO5S 详情 详情
(IX) 11303 (E)-3-Phenyl-2-propenoyl chloride; 3-Phenyl-2-propenoyl chloride 102-92-1 C9H7ClO 详情 详情
(X) 11304 2-Methyl-1,1-dioxo-4-[[(E)-3-phenyl-2-propenoyl]oxy]-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylic (E)-2-phenyl-2-propenoic anhydride C28H21NO7S 详情 详情
(XI) 11305 2-Pyridinamine; 2-Pyridinylamine; 2-Aminopyridine 504-29-0 C5H6N2 详情 详情
(XII) 11306 Cyclohexanol 108-93-0 C6H12O 详情 详情
(XIII) 11307 cyclohexyl 2-chloroacetate C8H13ClO2 详情 详情
(XIV) 11308 cyclohexyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate C15H17NO5S 详情 详情
(XV) 11309 cyclohexyl 4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C15H17NO5S 详情 详情
(XVI) 11310 cyclohexyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate C16H19NO5S 详情 详情
Extended Information