HRID1280868

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID11430

Potassium Carbonate

CK2O3

HCID53919072

未命名化合物

结构：CC(CCC(=O)O)C1CCC2C3C(O)CC4CC(OCCNC(=O)Cc5ccc(O)cc5)CCC4(C)C3CC(O)C12C

HCID69725368

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)C(C)=Cc1cc(F)c(Oc2ccc(CC(=O)NCCOC3CCC4(C)C(C3)CC(O)C3C4CC(O)C4(C)C(C(C)CCC(=O)O)CCC34)cc2)c(F)c1

HCID69726546

未命名化合物

收率 62.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 150 °C

PROCEDURE

实验过程

610 mg of 4-(7,12-dihydroxy-3-{2-[2-(4-hydroxyphenyl)acetylamino]ethoxy}-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl)pentanoic acid, 232 mg of ethyl 2-methyl-3-(3,4,5-trifluorophenyl)acrylate and 393 mg of K2CO3 are suspended in 5 ml of DMF (anhydrous) and the suspension is stirred at 150° C. for 160 minutes. After cooling, the reaction mixture is taken up using 150 ml of a 2N aqueous HCl solution and extracted three times using 100 ml of EA each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. Chromatography on silica gel using EA/MeOH 10:1 yields 480 mg of resinous product.

WORKUP

后处理

temperatureAfter cooling
extractionextracted three times
dry with materialThe extract is dried over Na2SO4
customthe solvent is removed in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d4b9aa4c49c34960b313b89001e25691
来源数据集: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06451781B1
来源说明: uspto-grants-2002_09

反应 SMILES

[OH:1][CH:2]1[CH:18]2[CH:10]([CH2:11][CH:12]([OH:27])[C:13]3([CH3:26])[CH:17]2[CH2:16][CH2:15][CH:14]3[CH:19]([CH3:25])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:9]2([CH3:28])[CH:4]([CH2:5][CH:6]([O:29][CH2:30][CH2:31][NH:32][C:33](=[O:42])[CH2:34][C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)[CH2:7][CH2:8]2)[CH2:3]1.[CH3:43][C:44](=[CH:50][C:51]1[CH:56]=[C:55]([F:57])[C:54](F)=[C:53]([F:59])[CH:52]=1)[C:45]([O:47][CH2:48][CH3:49])=[O:46].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[C:22]([CH2:21][CH2:20][CH:19]([CH:14]1[C:13]2([CH3:26])[CH:17]([CH:18]3[CH:10]([CH2:11][CH:12]2[OH:27])[C:9]2([CH3:28])[CH:4]([CH2:5][CH:6]([O:29][CH2:30][CH2:31][NH:32][C:33]([CH2:34][C:35]4[CH:36]=[CH:37][C:38]([O:41][C:54]5[C:53]([F:59])=[CH:52][C:51]([CH:50]=[C:44]([CH3:43])[C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:56][C:55]=5[F:57])=[CH:39][CH:40]=4)=[O:42])[CH2:7][CH2:8]2)[CH2:3][CH:2]3[OH:1])[CH2:16][CH2:15]1)[CH3:25])([OH:24])=[O:23]