【结 构 式】 |
【分子编号】50929 【品名】 【CA登记号】 |
【 分 子 式 】C16H14N2O3 【 分 子 量 】282.29884 【元素组成】C 68.08% H 5% N 9.92% O 17% |
合成路线1
该中间体在本合成路线中的序号:(IV)The precursor acid chloride (VII) was synthesized from isophthalic acid (I) as follows: Treatment of the triethylammonium salt of (I) with benzyl bromide provided the mono-benzyl ester (II). Acid chloride (III) was then formed by reaction of (II) with oxalyl chloride in the presence of a catalytic amount of DMF. Arndt-Eistert homologation of (III) to produce (VI) was achieved via reaction with diazomethane to yield the intermediate diazo ketone (IV). Wolff rearrangement of diazo ketone (IV) in the presence of Ag2O in hot trichloroethanol furnished the trichloroethyl ester (V). Reductive cleavage of the trichloroethyl ester group of (V) with Zn and HOAc then gave the carboxylic acid (VI). This was subsequently activated as the acid chloride (VII) by using oxalyl chloride and DMF.
【1】 Adlington, R.M.; Baldwin, J.E.; Becker, G.W.; et al.; Design, synthesis, and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen. J Med Chem 2001, 44, 10, 1491. |
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) | 50926 | m-Phthalic acid; Isophthalic acid; Benzene-1,3-dicarboxylic acid; 1,3-Benzenedicarboxylic acid | 121-91-5 | C8H6O4 | 详情 | 详情 |
(II) | 50927 | 3-[(benzyloxy)carbonyl]benzoic acid | C15H12O4 | 详情 | 详情 | |
(III) | 50928 | benzyl 3-(chlorocarbonyl)benzoate | C15H11ClO3 | 详情 | 详情 | |
(IV) | 50929 | C16H14N2O3 | 详情 | 详情 | ||
(V) | 50930 | benzyl 3-[2-oxo-2-(2,2,2-trichloroethoxy)ethyl]benzoate | C18H15Cl3O4 | 详情 | 详情 | |
(VI) | 50931 | 2-[3-[(benzyloxy)carbonyl]phenyl]acetic acid | C16H14O4 | 详情 | 详情 | |
(VII) | 50932 | benzyl 3-(2-chloro-2-oxoethyl)benzoate | C16H13ClO3 | 详情 | 详情 |