• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】12310

【品名】methyl 2-(2,8-diisopropyl-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetate

【CA登记号】

【 分 子 式 】C17H23NO4

【 分 子 量 】305.37396

【元素组成】C 66.86% H 7.59% N 4.59% O 20.96%

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)

The cyclization of 2-amino-6-isoproylphenol (I) with 2-bromo-3-methylbutyryl chloride (II) by means of NaHCO3 in ethyl acetate - water gives 2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one (III), which is condensed with methyl bromoacetate (IV) by means of NaH in DMF yielding 2,8-diisopropyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-4-acetic acid methyl ester (V). The reaction of (V) with P2S5 in refluxing toluene affords the corresponding thioxo derivative (VI), which is finally hydrolyzed with NaOH in dioxane - methanol.

1 Meguro, K.; Ikeda, H.; Yamamoto, Y. (Senju Pharmaceuticals Co., Ltd.; Takeda Chemical Industries, Ltd.); Thiolactam-N-acetic acid derivs., their production and use. EP 0243018; JP 1988107970; US 4771050 .
2 Prous, J.; Castaner, J.; AD-5467. Drugs Fut 1991, 16, 1, 13.
3 Ikeda, H.; Meguro, K.; Yamamoto, Y.; Tawada, Sugiyama, Y.; Studies on antidiabetic agents. IX. A new aldose reductase inhibitor, AD-5467, and related 1,4-benzoxazine and 1,4-benzothiazine derivatives: Synthesis and biological activity. Chem Pharm Bull 1990, 38, 5, 1238-45.
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) 12306 2-Amino-6-isopropylphenol C9H13NO 详情 详情
(II) 12307 alpha-Bromoisovaleryl chloride; 2-Bromo-3-methylbutanoyl chloride 52574-82-0 C5H8BrClO 详情 详情
(III) 12308 2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one C14H19NO2 详情 详情
(IV) 12309 methyl 2-bromoacetate; methyl bromoacetate 96-32-2 C3H5BrO2 详情 详情
(V) 12310 methyl 2-(2,8-diisopropyl-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetate C17H23NO4 详情 详情
(VI) 12311 methyl 2-(2,8-diisopropyl-3-thioxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetate C17H23NO3S 详情 详情
Extended Information