HRID1837237

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID12017057

未命名化合物

结构：CNCCCCC[C@@H]1Cc2cc(O)ccc2[C@@H]2[C@@H]1[C@@H]1CCC(=O)[C@@]1(C)C[C@@H]2F

HCID15870665

未命名化合物

PRODUCTS

生成物

结构：CN(CCCCC[C@@H]1Cc2cc(O)ccc2[C@@H]2[C@@H]1[C@@H]1CCC(=O)[C@@]1(C)C[C@@H]2F)CCCC(F)(F)C(F)(F)F

HCID15870669

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6569

Methyl ethyl ketone

C4H8O

PROCEDURE

实验过程

500 mg of 11β-fluoro-3-hydroxy-7α-(5-(methyl-amino)-pentyl)-estra-1,3,5(10)-trien-17-one is dissolved in 15 ml of ethylmethylketone, mixed with 1.1 g of potassium carbonate and 1.5 ml of 1,1,1,2,2-pentafluor-5-iodo-pentane and refluxed for 2.5 hours. For working-up, the reaction mixture is cooled to room temperature, stirred into saturated common salt solution, extracted with ethyl acetate, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Preparative column chromatography on silica gel with a methylene chloride-methanol gradient provides 397 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one.

WORKUP

后处理

temperaturerefluxed for 2.5 hours
extractionextracted with ethyl acetate
customdried on magnesium sulfate
concentrationconcentrated by evaporation in a vacuum

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ea087405f3954a98ae5272adb2d3655b
来源数据集: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06780855B2
来源说明: uspto-grants-2004_08

反应 SMILES

[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].[F:35][C:36]([F:45])([F:44])[C:37]([F:43])([F:42])[CH2:38][CH2:39][CH2:40]I>C(C(C)=O)C>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:27])[CH2:40][CH2:39][CH2:38][C:37]([F:43])([F:42])[C:36]([F:45])([F:44])[F:35]