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【结 构 式】

【分子编号】61729

【品名】4-nitrobenzyl 7-azido-2-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-2-(methylsulfanyl)-4-oxoazetidinyl]-4,4-dimethyl-3-oxoheptanoate

【CA登记号】

【 分 子 式 】C22H29N5O7S

【 分 子 量 】507.56776

【元素组成】C 52.06% H 5.76% N 13.8% O 22.07% S 6.32%

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:(VII)

The reaction of azetidinone (I) with sodium methyl mercaptan in acetonitrile gives the methylsulfanyl derivative (II), which is alkylated with para-methoxybenzyl 2-iodoacetate (III) by means of BuLi in THF to yield the azetidine-acetic acid derivative (IV). The acylation of (IV) with 5-azido-2,2-dimethylpentanoyl chloride (V) by means of LiHMDS affords the beta-oxopentanoate (VI), which is desilylated by means of TBAF and AcOH in THF to provide the 1-hydroxyethyl-azetidine (VII). The reaction of (VII) with chlorine or methyl sulphenyl chloride furnishes the chloroazetidine (VIII), which, without isolation, is cyclized by means of TEA in THF to give the precursor (IX). Finally, this compound is submitted to hydrogenation with H2 over Pd/C to provide the target aminoacid.

1 Simpson, I.N.; et al.; Broad-spectrum beta-lactamase inhibitor AM-112: Synthesis and enhancement of the in vitro activity of ceftazidime and piperacillin. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-345.
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) 11687 (2R,3R)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetanyl acetate C13H25NO4Si 详情 详情
(II) 61726 (3S,4R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-(methylsulfanyl)-2-azetidinone C12H25NO2SSi 详情 详情
(III) 54841 4-nitrobenzyl 2-iodoacetate C9H8INO4 详情 详情
(IV) 54842 4-nitrobenzyl 2-[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(methylsulfanyl)-4-oxoazetidinyl]acetate C21H32N2O6SSi 详情 详情
(V) 61727 5-azido-2,2-dimethylpentanoyl chloride C7H12ClN3O 详情 详情
(VI) 61728 4-nitrobenzyl 7-azido-2-[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(methylsulfanyl)-4-oxoazetidinyl]-4,4-dimethyl-3-oxoheptanoate C28H43N5O7SSi 详情 详情
(VII) 61729 4-nitrobenzyl 7-azido-2-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-2-(methylsulfanyl)-4-oxoazetidinyl]-4,4-dimethyl-3-oxoheptanoate C22H29N5O7S 详情 详情
(VIII) 61730 4-nitrobenzyl 7-azido-2-{(3S)-2-chloro-3-[(1R)-1-hydroxyethyl]-4-oxoazetidinyl}-4,4-dimethyl-3-oxoheptanoate C21H26ClN5O7 详情 详情
(IX) 61731 4-nitrobenzyl (5R,6R)-3-(5-azido-1,1-dimethylpentyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C22H27N5O7 详情 详情
Extended Information