HRID2181773

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1118

Sulfuric acid

H2O4S

HCID7914

Isopropyl ether

C6H14O

HCID11430

Potassium Carbonate

CK2O3

HCID13564

ETHANOL, 2-BROMO-, ACETATE

C4H7BrO2

$结构：CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1$

HCID5479529

Cefuroxime

C16H16N4O8S

PRODUCTS

生成物

$结构：CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OC(C)OC(C)=O)=C(COC(N)=O)CS[C@H]12)c1ccco1$

HCID6321416

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID8007

Butylamine

C4H11N

溶剂HCID31374

Dimethylacetamide

C4H9NO

3 次

溶剂HCID516892

Sodium Bicarbonate

CHNaO3

PROCEDURE

实验过程

11.14 g of cefuroxime in the form of a salt with n-butylamine are dissolved at ca. 3° to 5° in 28 ml of dimethyl acetamide. A solution of 7.48 g of acetoxyethyl bromide in 21 ml of dimethyl acetamide is added to the solution obtained, and 1.76 g of K2CO3 are added in portions over the course of ca. 120 minutes. The resulting mixture is stirred for ca. 30 minutes, diluted with 100 ml of EtAc and aqueous 3% NaHCO3 solution is added. Two phases are formed and are separated and the organic phase is washed with 1 n HCl and 20% aqueous NaCl solution, which contains 2% NaHCO3. The organic phase obtained is mixed with 11 ml of dimethyl acetamide and 28 ml of H2O, and the pH of the mixture obtained is adjusted to ca. 4 by addition of H2SO4. The two phases formed are separated and the organic phase is mixed with activated carbon, which is filtrated off. From the filtrate obtained solvent is evaporated off and the evaporation residue obtained is mixed with seed crystals. The suspension obtained is mixed with 125 ml of diisopropyl ether and stirred at room temperature. Crystalline cefuroxime axetil is obtained, filtrated off, washed with a mixture of EtAc and diisopropyl ether and dried. Yield: 7.43 g.

WORKUP

后处理

customobtained
additionis added
customTwo phases are formed
customare separated
washthe organic phase is washed with 1 n HCl and 20% aqueous NaCl solution, which
customThe organic phase obtained
customthe pH of the mixture obtained
customThe two phases formed
customare separated
additionthe organic phase is mixed with activated carbon, which
filtrationis filtrated off
customFrom the filtrate obtained solvent
customis evaporated off
customthe evaporation residue obtained
additionis mixed with seed crystals
customThe suspension obtained
stirringstirred at room temperature

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cc9e21bd84a34c3fa252a37237e70df7
来源数据集: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06894162B2
来源说明: uspto-grants-2005_05

反应 SMILES

[CH3:1][O:2]/[N:3]=[C:4](\[C:10]([NH:12][C@@H:13]1[C:16](=[O:17])[N:15]2[C:18]([C:27]([OH:29])=[O:28])=[C:19]([CH2:22][O:23][C:24]([NH2:26])=[O:25])[CH2:20][S:21][C@H:14]12)=[O:11])/[C:5]1[O:9][CH:8]=[CH:7][CH:6]=1.[C:30]([O:33][CH2:34][CH2:35]Br)(=[O:32])[CH3:31].C([O-])([O-])=O.[K+].[K+].OS(O)(=O)=O.C(OC(C)C)(C)C>C(N)CCC.CC(N(C)C)=O.C([O-])(O)=O.[Na+].O>[CH3:35][CH:34]([O:28][C:27]([C:18]1[N:15]2[C:16]([C@@H:13]([NH:12][C:10](/[C:4](/[C:5]3[O:9][CH:8]=[CH:7][CH:6]=3)=[N:3]\[O:2][CH3:1])=[O:11])[C@H:14]2[S:21][CH2:20][C:19]=1[CH2:22][O:23][C:24]([NH2:26])=[O:25])=[O:17])=[O:29])[O:33][C:30]([CH3:31])=[O:32]