HRID851567

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID11430

Potassium Carbonate

CK2O3

HCID11820084

未命名化合物

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

HCID12774332

未命名化合物

PRODUCTS

生成物

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

HCID178502900

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

2 次

PROCEDURE

实验过程

(6R,7R)-3-Acetoxymethyl-7-[Z-2-methoxycarbamoylmethoxyimino-2-(fur-2-yl)acetamido]-ceph-3-em-4-carboxylic acid (992 mg) was dissolved in dry N,N-dimethylformamide (8 ml). Dried potassium carbonate (138 mg) was added and the mixture was stirred at 0°. Iodomethyl acetate (1.1 g) in a little dimethylformamide was added, stirring was continued at 0° for 1 hr, and the mixture was poured into hydrochloric acid (N, 50 ml) and extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts were washed with N-hydrochloric acid (2×50 ml), water (100 ml) and saturated sodium hydrogen carbonate solution (2×30 ml), dried (Na2SO4) and evaporated. The residue in a little ethyl acetate was added dropwise to well-stirred light petroleum (b.p. 40°-60°), when the ester separated as an off-white powder, 513 mg, λmax (EtOH) 277.5 nm, νmax (Nujol) 3240 (--NH), 1786 (β-lactam), 1765, 1742 (acetate+--CO2CH2OCOCH3), 1680, 1540 cm-1 (--CONH--), τ(DMSOd6) 6.25 (--OCH3, 2--CH2 --), 5.38 (--O--CH2 --CO--), 2.01, 3.11, 3.22 (fur-2-yl), 0.18 (--CONH--), 4.05 (7H), 4.69 (6H), 4.99, 5.25 (3--CH2 --), 7.86, 7.96 (--COCH3), 4.09 (--OCH2O--).

WORKUP

后处理

stirringstirring
extractionextracted with ethyl acetate (3×50 ml)
washThe ethyl acetate extracts were washed with N-hydrochloric acid (2×50 ml), water (100 ml) and saturated sodium hydrogen carbonate solution (2×30 ml)
dry with materialdried (Na2SO4)
customevaporated
additionThe residue in a little ethyl acetate was added dropwise
stirringto well-stirred light petroleum (b.p. 40°-60°), when the ester
customseparated as an off-white powder, 513 mg, λmax (EtOH) 277.5 nm, νmax (Nujol) 3240 (--NH), 1786 (β-lactam), 1765, 1742 (acetate+--CO2CH2OCOCH3), 1680, 1540 cm-1 (--CONH--), τ(DMSOd6) 6.25 (--OCH3, 2--CH2 --), 5.38 (--O--CH2 --CO--), 2.01, 3.11, 3.22 (fur-2-yl), 0.18 (--CONH--), 4.05 (7H), 4.69 (6H), 4.99, 5.25 (3--CH2 --), 7.86, 7.96 (--COCH3), 4.09 (--OCH2O--)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e6708fb450494a5887ff817f40cf1f0e
来源数据集: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04385177
来源说明: uspto-grants-1983_05

反应 SMILES

[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:33])/[C:19](=[N:25]\[O:26][CH2:27][C:28](=[O:32])[NH:29][O:30][CH3:31])/[C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:34])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:41]([O:44][CH2:45]I)(=[O:43])[CH3:42].Cl>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:33])/[C:19](=[N:25]\[O:26][CH2:27][C:28](=[O:32])[NH:29][O:30][CH3:31])/[C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:34])[N:10]2[C:11]=1[C:12]([O:14][CH2:45][O:44][C:41](=[O:43])[CH3:42])=[O:13])(=[O:3])[CH3:2]