HRID1633748

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10220585

2-acetylamino-8-amino-6-fluoro-5-methyl-1-tetralone

C13H15FN2O2

结构：CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)CCC1=O

HCID10220900

(4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

C13H13NO5

PRODUCTS

生成物

结构：CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2c-1nc1cc(F)c(C)c3c1c2C(NC(C)=O)CC3

HCID12067229

未命名化合物

收率 91.4%

AUXILIARIES

试剂、催化剂与溶剂

结构：Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1

催化剂HCID466102

未命名化合物

3 次

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

To 2.00 g of 2-acetylamino-8-amino-6-fluoro-5-methyl-1-tetralone and 2.10 g of (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione, 250 ml of toluene and then 0.1 g of pyridinium p-toluenesulfonate were added, followed by heating under reflux for 3 hours. The mixture was added with 0.1 g of pyridinium p-toluenesulfonate, followed by heating under reflux for 2.5 hours. The mixture was then added with 0.1 g of pyridinium p-toluenesulfonate, followed by heating under reflux for 38 hours. The reaction mixture was cooled. The solvent was then removed under reduced pressure. To a crystalline residue, acetone was added and the crystals so precipitated were collected by filtration, whereby 3.48 g of the title compound were obtained.

WORKUP

后处理

temperatureby heating
temperatureunder reflux for 3 hours
temperatureby heating
temperatureunder reflux for 2.5 hours
temperatureby heating
temperatureunder reflux for 38 hours
temperatureThe reaction mixture was cooled
customThe solvent was then removed under reduced pressure
additionTo a crystalline residue, acetone was added
customthe crystals so precipitated
filtrationwere collected by filtration

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-725335c41bee44f49bf3ffa0c490a86e
来源数据集: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06504029B1
来源说明: uspto-grants-2003_01

反应 SMILES

[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([NH2:17])[CH:9]=[C:10]([F:16])[C:11]=2[CH3:15])[C:6]1=O)(=[O:3])[CH3:2].[CH2:19]([C@:21]1([OH:37])[C:33]2[CH:32]=[C:31]3[N:27]([CH2:28][CH2:29][C:30]3=O)[C:26](=[O:35])[C:25]=2[CH2:24][O:23][C:22]1=[O:36])[CH3:20]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([NH:4][CH:5]1[C:6]2=[C:29]3[CH2:28][N:27]4[C:31](=[CH:32][C:33]5[C@:21]([CH2:19][CH3:20])([OH:37])[C:22](=[O:36])[O:23][CH2:24][C:25]=5[C:26]4=[O:35])[C:30]3=[N:17][C:8]3[CH:9]=[C:10]([F:16])[C:11]([CH3:15])=[C:12]([C:7]=32)[CH2:13][CH2:14]1)(=[O:3])[CH3:2]