HRID1837232

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID516892

Sodium Bicarbonate

CHNaO3

结构：Cc1ccc(S(=O)(=O)OCCCCCCCC(F)(F)C(F)(F)F)cc1

HCID15858643

未命名化合物

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

HCID15870667

未命名化合物

PRODUCTS

生成物

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

HCID86587643

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A solution of 381 mg of 11β-fluoro-3-hydroxy-7α-[6-(methyl-amino)-hexyl]-estra-1,3,5(10)-trien-17-one in 5 ml of dimethylformamide is stirred with 200 mg of 8,8,9,9,9-pentafluorononyltosylate for 2 hours at a bath temperature of 100° C. Then, it is added to semi-saturated sodium bicarbonate solution, extracted three times with methylene chloride, dried on magnesium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane/methanol. 90 mg of 11β-fluoro-3-hydroxy-7α-{6-[methyl-(8,8,9,9,9-pentafluoro-nonyl)-amino]-hexyl}-estra-1,3,5(10)-trien-17-one is obtained as a foam.

WORKUP

后处理

extractionextracted three times with methylene chloride
customdried on magnesium sulfate
concentrationconcentrated by evaporation in a vacuum
customchromatographed on silica gel with dichloromethane/methanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-972e0a1e1d9b4aa3ac67709e94e1d55c
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:29])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][CH3:28].[F:30][C:31]([F:54])([C:50]([F:53])([F:52])[F:51])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]COS(C1C=CC(C)=CC=1)(=O)=O.[C:55](=O)(O)[O-].[Na+]>CN(C)C=O>[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:29])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:55])[CH2:28][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:31]([F:30])([F:54])[C:50]([F:51])([F:52])[F:53]