HRID442361

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10868

Dicyclohexylcarbodiimide

C13H22N2

HCID11600913

4-(HYDROXYMETHYL)PHENYL PIVALATE

C12H16O3

结构：CC(=O)OCC1=C(C(=O)O)N2C(=O)C(NC(=O)Cc3ccc(CN=[N+]=[N-])cc3)C2SC1.Cl

HCID86735042

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OCC1=C(C(=O)OCc2ccc(OC(=O)C(C)(C)C)cc2)N2C(=O)C(NC(=O)Cc3ccc(CN=[N+]=[N-])cc3)C2SC1

HCID54380599

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

To a solution of 1.8 of 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride in 25 ml of dimethyl formamide is added 0.78 g of p-pivalyloxybenzyl alcohol followed by cooling to 0° C after which 3.7 mole of dicyclohexylcarbodiimide in 7.5 ml of dimethyl formamide is added dropwise with stirring. The reaction mixture is stirred for 1 hour at 0° C. and for an additional 4 hours at room temperature. The formed dicyclohexylurea is removed by filtration. The filtrate is diluted with chloroform and washed with water. The organic layer is then dried over magnesium sulfate filtered and evaporated in vacuo to give an oil which is triturated with ether to give 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid p-pivalyloxybenzyl ester.

WORKUP

后处理

additionis added dropwise
stirringThe reaction mixture is stirred for 1 hour at 0° C. and for an additional 4 hours at room temperature
customThe formed dicyclohexylurea is removed by filtration
additionThe filtrate is diluted with chloroform
washwashed with water
dry with materialThe organic layer is then dried over magnesium sulfate
filtrationfiltered
customevaporated in vacuo
customto give an oil which
customis triturated with ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-49a212b854ec49b7860df88f2807d344
来源数据集: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04045438
来源说明: uspto-grants-1977_08

反应 SMILES

Cl.[C:2]([O:5][CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:29])[CH:11]2[NH:15][C:16](=[O:28])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]=[N+:26]=[N-:27])=[CH:20][CH:19]=2)[C:8]=1[C:30]([OH:32])=[O:31])(=[O:4])[CH3:3].[C:33]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44]O)=[CH:42][CH:41]=1)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:33]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][O:31][C:30]([C:8]2[N:9]3[CH:12]([S:13][CH2:14][C:7]=2[CH2:6][O:5][C:2](=[O:4])[CH3:3])[CH:11]([NH:15][C:16](=[O:28])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][N:25]=[N+:26]=[N-:27])=[CH:22][CH:23]=2)[C:10]3=[O:29])=[O:32])=[CH:42][CH:41]=1)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]