炔诺孕酮 → (3E)-17-Deacetylnorgestimate

HRID 1160801

反应方程式

HRID 1160801 反应方程式
[CH3:1][CH2:2][C@@:3]12[C@:11]([OH:14])([C:12]#[CH:13])[CH2:10][CH2:9][C@H:8]1[C@@H:7]1[CH2:15][CH2:16][C:17]3[C@@H:23]([C@H:6]1[CH2:5][CH2:4]2)[CH2:22][CH2:21][C:19](=O)[CH:18]=3.C([C@]12CC[C@@H]3C4CC=C(OC)CC=4CC[C@H]3[C@@H]1CC[C@@H]2O)C.[Cl-].O[NH3+].C([C@]12CC[C@@H]3[C@@H]4C(CC[C@H]3[C@@H]1CC[C@@H]2O)=CC(=[N:68][OH:69])CC4)C>N1C=CC=CC=1>[CH3:1][CH2:2][C@@:3]12[C@:11]([OH:14])([C:12]#[CH:13])[CH2:10][CH2:9][C@H:8]1[C@@H:7]1[CH2:15][CH2:16][C:17]3[C@@H:23]([C@H:6]1[CH2:5][CH2:4]2)[CH2:22][CH2:21]/[C:19](=[N:68]\[OH:69])/[CH:18]=3

参与物

6

反应物 4

HCID 13109炔诺孕酮HCID 21645盐酸羟胺HCID 101950左炔诺孕酮杂质QHCID 8659645113-Ethyl-3-(hydroxyimino)-gon-4-ene-17beta-ol

产物 1

HCID 9568628(3E)-17-Deacetylnorgestimate

试剂、催化剂与溶剂 1

HCID 1049吡啶溶剂

实验过程

Hungarian Patent No. 165356 describes the synthesis of dl- as well as d-norgestrel. The starting material of the synthesis is the racemic or the optically active 13-ethyl-3-methoxygona-2,5(10)-diene-17β-ol, which is reacted with hydroxylammonium chloride in pyridine at 100° C. Then the obtained 13-ethyl-3-(hydroxyimino)-gon-4-ene-17β-ol is oxidized at position 17, followed by ethinylation of the oxo group at position 17, to give the dl-(17α)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime, or norelgestromin. Although the synthesis of the intermediates, the dl-(17α)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime and norelgestromin, are described, the identification and the purity (the quality requirements) as well as the pharmacological activity of these compounds are not provided.

来源与证据

ORD记录
ord-6fc91d3964df413fb7a6b740b57eb5b2
来源数据集
uspto-grants-2010_10
专利号
US07816546B2

关联笔记

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