HRID1702735

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID5238

Sodium Iodide

INa

2 次

HCID8471

Triethylamine

C6H15N

HCID70320

2-Bromomethylnaphthalene

C11H9Br

2 次

HCID516893

Potassium bicarbonate

CHKO3

2 次

结构：CCN1CCN(C(=O)NC(C(=O)NC2C(=O)N3C(C(=O)O)=C(C)CS[C@H]23)c2ccccc2)C(=O)C1=O

HCID70507310

未命名化合物

PRODUCTS

生成物

结构：CCN1CCN(C(=O)NC(C(=O)NC2C(=O)N3C(C(=O)OCc4ccc5ccccc5c4)=C(C)CS[C@H]23)c2ccccc2)C(=O)C1=O

HCID70508548

未命名化合物

收率 84.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID180

Acetone

C3H6O

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

3-Methyl-7-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]ceph-3-em-4-carboxylic acid (4.48 g., 8.7 mmoles) was dissolved in 30 ml. of dimethylformamide. Triethylamine (8.79 mg., 8.7 mmoles) was added and the mixture stirred for 30 minutes. Potassium bicarbonate (1.74 g., 17.4 mmoles) was added and stirring continued for 1 hour. Finally sodium iodide (1.3 g., 8.7 mmoles) and 2-(bromomethyl)naphthalene (2.11 g., 9.6 mmoles) were added (a slight exotherm was noted), and the mixture allowed to stir about 16 hours at room temperature. Since tlc (9:1 acetone:water) monitoring of the reaction mixture over the next 8 hours indicated that reaction had ceased prior to complete conversion to the ester, one-tenth quantities of potassium bicarbonate, sodium iodide and 2-(bromomethyl)naphthalene were added and the reaction allowed to proceed for a further 16 hours. The reaction mixture was diluted with 1:1 ethyl acetate:water, and the organic layer was separated and back-washed several times with water. The organic phase was layered with fresh water, the pH lowered to 2.5, and the organic layer separated, washed with several portions of water, washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to yield 2-naphthylmethyl 3-methyl-7-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]ceph-3-em-4-carboxylate [4.8 g., 84%; Rf 0.39 (ethyl acetate)].

WORKUP

后处理

stirringstirring
waitcontinued for 1 hour
stirringto stir about 16 hours at room temperature
additionwere added
waitto proceed for a further 16 hours
customwater, and the organic layer was separated
washback-washed several times with water
customthe organic layer separated
washwashed with several portions of water
washwashed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f4d1f64f12ff47d3863582ff11659c45
来源数据集: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04348264
来源说明: uspto-grants-1982_09

反应 SMILES

[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14](=[O:35])[CH:15]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[NH:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[C:21](=[O:27])[C:20]3=[O:28])=[O:18])[C:11](=[O:36])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].C(N(CC)CC)C.C(=O)(O)[O-].[K+].[I-].[Na+].Br[CH2:52][C:53]1[CH:62]=[CH:61][C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH:54]=1>C(OCC)(=O)C.O.CC(C)=O.CN(C)C=O>[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14](=[O:35])[CH:15]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[C:21](=[O:27])[C:20]3=[O:28])=[O:18])[C:11](=[O:36])[N:6]2[C:7]=1[C:8]([O:10][CH2:52][C:53]1[CH:62]=[CH:61][C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH:54]=1)=[O:9]