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【结 构 式】

【分子编号】58727

【品名】(2R,3S)-3-amino-2-methyl-4-oxo-1-azetidinesulfonic acid

【CA登记号】

【 分 子 式 】C4H8N2O4S

【 分 子 量 】180.1846

【元素组成】C 26.66% H 4.48% N 15.55% O 35.52% S 17.8%

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:(XII)

2-Formamido-4-thiazolecarboxylic acid (X) was activated as the mixed anhydride (XI) upon treatment with pivaloyl chloride and triethylamine. Subsequent coupling of anhydride (XI) with the aminoazetidinesulfonic acid (XII) provided the corresponding amide, which was further converted to the tetrabutylammonium sulfamate salt (XIII). The condensation between the keto group of (XIII) and hydroxylamine (IX) gave rise to the corresponding oxime (XIV). Finally, acid hydrolysis of the N-formyl group of (XIV) furnished the title compound.

1 Koster, W.H.; Sundeen, J.E.; Straub, H.; Ermann, P.H.; Treuner, U. (Bristol-Myers Squibb Co.); Heteroaroyl derivs. of monocyclic beta-lactam antibiotics. EP 0484881; JP 1992283579 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 58725 3-[(aminooxy)methyl]-6,7-dihydroxy-2-quinoxalinecarboxylic acid C10H9N3O5 详情 详情
(X) 31132 2-[2-(formylamino)-1,3-thiazol-4-yl]-2-oxoacetic acid C6H4N2O4S 详情 详情
(XI) 58726 1,1-dimethylpropanoic [2-(formylamino)-1,3-thiazol-4-yl](oxo)acetic anhydride C11H12N2O5S 详情 详情
(XII) 58727 (2R,3S)-3-amino-2-methyl-4-oxo-1-azetidinesulfonic acid C4H8N2O4S 详情 详情
(XIII) 58728 N,N,N-tributyl-1-butanaminium (2R,3S)-3-({2-[2-(formylamino)-1,3-thiazol-4-yl]-2-oxoacetyl}amino)-2-methyl-4-oxo-1-azetidinesulfonate C26H45N5O7S2 详情 详情
(XIV) 58729 disodium 3-({[((Z)-1-[2-(formylamino)-1,3-thiazol-4-yl]-2-{[(2R,3S)-2-methyl-4-oxo-1-sulfonatoazetidinyl]amino}-2-oxoethylidene)amino]oxy}methyl)-6,7-dihydroxy-2-quinoxalinecarboxylate C20H15N7Na2O11S2 详情 详情
Extended Information