HRID1659564

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

结构：CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O

HCID11082

6-Aminopenicillanic acid

C8H12N2O3S

结构：Cc1ccc(OC(=O)C(C(=O)Oc2c(Cl)c(Cl)c(Cl)c(Cl)c2Cl)c2ccccc2)cc1C

HCID54238210

未命名化合物

PRODUCTS

生成物

结构：CC[NH+](CC)CC.Cc1ccc(OC(=O)C(C(=O)NC2C(=O)N3C(C(=O)[O-])C(C)(C)S[C@H]23)c2ccccc2)cc1C

HCID131711638

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

CONDITIONS

反应条件

温度: 0 °C

PROCEDURE

实验过程

3.6 ml. (0.026 moles) of triethylamine are added to a suspension of 2.8 g. (0.013 moles) of 6-APA in 50 ml. of dichloromethane, and the mixture is stirred at room temperature until a clear solution is obtained. The solution is cooled to 0° C., 7 g. (0.013 moles) of phenylmalonic acid 3,4-dimethylphenylester pentachlorophenylester are added, and the mixture is stirred at the same temperature for one hour. Thereafter the solvent is evaporated in vacuo, and the residue is admixed with 30 ml. of ethyl acetate. 7.5 g (95%) of 6-(α-[3,4-dimethylphenoxycarbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid triethylammonium salt separate in the form of a white, crystalline substance. M.p.: 155°-160° C.

WORKUP

后处理

customis obtained
customThereafter the solvent is evaporated in vacuo
custom7.5 g (95%) of 6-(α-[3,4-dimethylphenoxycarbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid triethylammonium salt separate in the form of a white, crystalline substance

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ac9c283872294394b2a48454a2652cd1
来源数据集: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04304717
来源说明: uspto-grants-1981_12

反应 SMILES

[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:8][C:9]1([CH3:21])[S:13][C@@H:12]2[C@H:14]([NH2:17])[C:15](=[O:16])[N:11]2[C@H:10]1[C:18]([OH:20])=[O:19].ClC1C([O:29][C:30](=O)[CH:31]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:32]([O:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([CH3:42])[CH:36]=2)=[O:33])=C(Cl)C(Cl)=C(Cl)C=1Cl>ClCCl>[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:42][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][C:38]=1[CH3:41])[O:34][C:32]([CH:31]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:30]([NH:17][CH:14]1[C:15](=[O:16])[N:11]2[CH:10]([C:18]([O-:20])=[O:19])[C:9]([CH3:21])([CH3:8])[S:13][C@H:12]12)=[O:29])=[O:33]