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【结 构 式】

【分子编号】56415

【品名】(2R,3S)-1-[tert-butyl(dimethyl)silyl]-3-(2-ethoxybenzyl)-4-oxo-2-azetidinecarboxylic acid

【CA登记号】

【 分 子 式 】C19H29NO4Si

【 分 子 量 】363.5291

【元素组成】C 62.78% H 8.04% N 3.85% O 17.6% Si 7.73%

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:(III)

Alkylation of the dianion of azetidinonecarboxylic acid (I) with 2-ethoxybenzyl bromide (II) in cold THF affords (III). Oxidative cleavage of the carboxyl group of (III) using lead tetraacetate and HOAc provides the acetate ester (IV), which is desilylated to (V) with tetrabutylammonium fluoride in THF. Azetidinone (V) is coupled with benzhydryl 4-hydroxybenzoate (VI) to yield ether (VII). Curtius rearrangement of carboxylic acid (VIII) provides isocyanate (IX). Coupling between isocyanate (IX) and azetidine (VII) gives rise to urea (X). The benzhydryl ester group of (X) is finally cleaved by treatment with trifluoroacetic acid in the presence of anisole.

1 Nakajima, M.; Kii, M.; Uenaka, M. (Shionogi & Co. Ltd.); Monocyclic beta-lactam cpds. and chymase inhibitors containing the same. EP 1099690; WO 0005204 .
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) 28418 (2R)-1-[tert-butyl(dimethyl)silyl]-4-oxo-2-azetidinecarboxylic acid C10H19NO3Si 详情 详情
(II) 56414 2-(bromomethyl)phenyl ethyl ether; 1-(bromomethyl)-2-ethoxybenzene C9H11BrO 详情 详情
(III) 56415 (2R,3S)-1-[tert-butyl(dimethyl)silyl]-3-(2-ethoxybenzyl)-4-oxo-2-azetidinecarboxylic acid C19H29NO4Si 详情 详情
(IV) 56416 (2S,3S)-1-[tert-butyl(dimethyl)silyl]-3-(2-ethoxybenzyl)-4-oxoazetidinyl acetate C20H31NO4Si 详情 详情
(V) 56417 (2S,3S)-3-(2-ethoxybenzyl)-4-oxoazetidinyl acetate C14H17NO4 详情 详情
(VI) 56418 benzhydryl 4-hydroxybenzoate C20H16O3 详情 详情
(VII) 56419 benzhydryl 4-{[(2S,3S)-3-(2-ethoxybenzyl)-4-oxoazetidinyl]oxy}benzoate C32H29NO5 详情 详情
(VIII) 43492 2-chloro-4-fluorobenzonitrile 60702-69-4 C7H3ClFN 详情 详情
(IX) 56420 1-[isocyanato(4-methylphenyl)methyl]-4-methylbenzene; bis(4-methylphenyl)methyl isocyanate C16H15NO 详情 详情
(X) 56421 benzhydryl 4-{[(2S,3S)-1-({[bis(4-methylphenyl)methyl]amino}carbonyl)-3-(2-ethoxybenzyl)-4-oxoazetidinyl]oxy}benzoate C48H44N2O6 详情 详情
Extended Information