HRID1707192

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1049

Pyridine

C5H5N

HCID8502

4-Nitrobenzoyl chloride

C7H4ClNO3

反应SMILES：CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=O)C(=NO)c3ccccc3)[C@H]2SC1

HCID131710762

未命名化合物

PRODUCTS

产物

反应SMILES：CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=O)C(=NOC(=O)c3ccc([N+](=O)[O-])cc3)c3ccccc3)[C@H]2SC1

HCID131710763

未命名化合物

收率 66.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

To a solution of diphenylmethyl 3-acetoxymethyl-7β-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylate (syn-isomer) (1.5 g.) and pyridine (0.5 ml.) in ethylacetate (100 ml.) was added 4-nitrobenzoyl chloride (0.42 g) and the resulting solution was stirred at room temperature for one hour. Further portions (0.042 g 0.015 g and 0.20 g.) of the acid chloride were added, and the reaction stirred for a total of 4 hours at room temperature. Then the solution was washed with 2 N-hydrochloric acid and brine, dried, concentrated to ca. 5 ml. and added dropwise with stirring to petroleum spirit (b.p. 40°-60°). This gave a solid which was filtered and dried, yielding the title ester (1.1 g; 58%), λmax. (EtOH) 263 nm (ε 29,000), νmax. (CHBr3) 3400 (NH), 1780 (β-lactam), 1395 and 1525 (NO2), 1687 and 1515 cm.- 1 (CONH), τ (CDCl3) values include 1.70 and 2.71 (two doublets, J 8 Hz; ##STR33## 2.1-2.85 (multiplet; aromatic protons), 8.03 (singlet; OCOCH3)

WORKUP

后处理

stirringthe reaction stirred for a total of 4 hours at room temperature
washThen the solution was washed with 2 N-hydrochloric acid and brine
customdried
concentrationconcentrated to ca. 5 ml
additionand added dropwise
stirringwith stirring to petroleum spirit (b.p. 40°-60°)
customThis gave a solid which
filtrationwas filtered
customdried

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-e898b4c5c2044330880291e5d49c7e84
来源数据集: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US04209616
来源说明: uspto-grants-1980_06

反应SMILES

[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:29]([NH:30][C:31](=[O:41])[C:32](=[N:39][OH:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:28](=[O:42])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2].N1C=CC=CC=1.[N+:49]([C:52]1[CH:60]=[CH:59][C:55]([C:56](Cl)=[O:57])=[CH:54][CH:53]=1)([O-:51])=[O:50]>C(OC(=O)C)C>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:29]([NH:30][C:31](=[O:41])[C:32](=[N:39][O:40][C:56](=[O:57])[C:55]3[CH:54]=[CH:53][C:52]([N+:49]([O-:51])=[O:50])=[CH:60][CH:59]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:28](=[O:42])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13])(=[O:3])[CH3:2]