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【结 构 式】

【分子编号】39926

【品名】methyl 2-(11-oxo-6,11-dihydrodibenzo[b,e]thiepin-3-yl)acetate

【CA登记号】

【 分 子 式 】C17H14O3S

【 分 子 量 】298.36236

【元素组成】C 68.44% H 4.73% O 16.09% S 10.75%

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:(IX)

The esterification of 2-nitroterephthalic acid (I) with isopropanol by means of dry HCl gives the corresponding dusoproyl ester (II), which by reaction with benzylmercaptane by means of NaH in DMF yields diisopropyl 2-benzylthioterephthalate (III). This compound is hydrolyzed with KOH in refluxing methanol affording the correspon-ding acid (IV), which is converted into its diacid chloride (V) by treatment with refluxing SOCl2. The cyclization of (V) with AlCl3 in methylene chloride - nitromethane affords 6,11-dihydrodibenzo[b]thiepin-11-one-3-carbonyl chloride (VI), which is treated with diazomethane in ether - methylene chloride to yield the 3-diazoacetyl derivative (VII). The Arndt-Eister reaction of (VII) with silver benzoate in refluxing methanol affords methyl 6,11-dihydrodibenzo[b,e]thiepin-11-one-3-acetate (VIII), which is finally hydrolyzed with KOH in refluxing methanol.

1 Castañer, J.; Leeson, P.; Tiopinac. Drugs Fut 1978, 3, 12, 896.
2 Ackrell, J. (Syntex (USA), Inc.); 6,11-Dihydrodibenzothiepin-11-ones, compositions and uses thereof. US 4000308 .
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) 39919 2-nitroterephthalic acid 610-29-7 C8H5NO6 详情 详情
(II) 39920 diisopropyl 2-nitroterephthalate C14H17NO6 详情 详情
(III) 21110 benzylhydrosulfide; phenylmethanethiol 100-53-8 C7H8S 详情 详情
(IV) 39921 diisopropyl 2-(benzylsulfanyl)terephthalate C21H24O4S 详情 详情
(V) 39922 2-(benzylsulfanyl)terephthalic acid C15H12O4S 详情 详情
(VI) 39923 3-(benzylsulfanyl)benzoyl chloride C14H11ClOS 详情 详情
(VII) 39924 11-oxo-6,11-dihydrodibenzo[b,e]thiepine-3-carbonyl chloride C15H9ClO2S 详情 详情
(VIII) 39925 3-(2-diazoacetyl)dibenzo[b,e]thiepin-11(6H)-one C16H10N2O2S 详情 详情
(IX) 39926 methyl 2-(11-oxo-6,11-dihydrodibenzo[b,e]thiepin-3-yl)acetate C17H14O3S 详情 详情
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