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【结 构 式】

【分子编号】24083

【品名】7-[[2-[[2-(tert-butoxy)-2-oxoethoxy]imino]-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

【CA登记号】

【 分 子 式 】C18H20N4O7S2

【 分 子 量 】468.51156

【元素组成】C 46.15% H 4.3% N 11.96% O 23.9% S 13.69%

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)

The condensation of 2-(tert-butoxycarbonylmethoxyimino)-2-(4 thiazolyl)acetic acid (I) with 7-amino 3-cephem-4-carboxylic acid (II) by means of the Vusmejer reagent (POCl3 and dimethylformamide) in ethyl acetate gives 7-[2-(tert-butoxycarbonylmethoxyimino)-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid (III), which is then de protected with trifluoroacetic acid and anisole in methylene chloride. The starting acetic acid derivative (I) can be obtained by several different ways: 1) The partial hydrolysis of 2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4yl) acetic acid (IV) with concentrated HCl in methanol gives 2-(tert-butoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetic acid (V), which is then deaminated with tert butyl nitrite in refluxing THF. 2) The preceding deamination of (IV) can be performed in a similar way with previous esterification with diphenyldiazomethane, through compounds (VI), (VII) and (VIII). Compound (VIII) is submitted to a partial hydrolysis with trifluoroacetic acid. 3) Compound (I) can also be obtained by condensation of 2-(4-thiazolylglyoxylic acid (IX) with tert-butyl-2-(aminooxy)acetate (X) by means of NaHCO3 in ethyl acetate.

1 Takaya, T.; Takasugi, H.; Yamanaka, H. (Fujisawa Pharmaceutical Co., Ltd.); Cephem compounds. EP 0071891; US 4515788; US 4649136; US 4736039 .
2 Prous, J.; Castaner, J.; FK-089. Drugs Fut 1986, 11, 2, 103.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
23767 Methoxybenzene; Methyl phenyl ether; Anisole 100-66-3 C7H8O 详情 详情
(A) 23003 Diphenyldiazomethane C13H10N2 详情 详情
(I) 24081 2-[[2-(tert-butoxy)-2-oxoethoxy]imino]-2-(1,3-thiazol-4-yl)acetic acid C11H14N2O5S 详情 详情
(II) 24082 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C7H8N2O3S 详情 详情
(III) 24083 7-[[2-[[2-(tert-butoxy)-2-oxoethoxy]imino]-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C18H20N4O7S2 详情 详情
(IV) 24084 2-[[2-(tert-butoxy)-2-oxoethoxy]imino]-2-[2-(formylamino)-1,3-thiazol-4-yl]acetic acid C12H15N3O6S 详情 详情
(V) 24085 2-(2-amino-1,3-thiazol-4-yl)-2-[[2-(tert-butoxy)-2-oxoethoxy]imino]acetic acid C11H15N3O5S 详情 详情
(VI) 24086 benzhydryl 2-[[2-(tert-butoxy)-2-oxoethoxy]imino]-2-[2-(formylamino)-1,3-thiazol-4-yl]acetate C25H25N3O6S 详情 详情
(VII) 24087 benzhydryl 2-(2-amino-1,3-thiazol-4-yl)-2-[[2-(tert-butoxy)-2-oxoethoxy]imino]acetate C24H25N3O5S 详情 详情
(VIII) 24088 benzhydryl 2-[[2-(tert-butoxy)-2-oxoethoxy]imino]-2-(1,3-thiazol-4-yl)acetate C24H24N2O5S 详情 详情
(IX) 24089 2-oxo-2-(1,3-thiazol-4-yl)acetic acid C5H3NO3S 详情 详情
(X) 24090 tert-butyl 2-(aminooxy)acetate C6H13NO3 详情 详情
Extended Information