Ethanol → Clarithromycin

HRID 2211583

反応式

HRID 2211583 の反応式
[CH3:1][CH2:2][C@H:3]1[O:19][C:17](=[O:18])[C@H:16]([CH3:20])[C@@H:15]([O:21][C@@H:22]2[O:27][C@@H:26]([CH3:28])[C@H:25]([OH:29])[C@@:24]([O:31][CH3:32])([CH3:30])[CH2:23]2)[C@H:14]([CH3:33])[C@@H:13]([O:34][C@@H:35]2[O:40][C@H:39]([CH3:41])[CH2:38][C@H:37]([N:42]([CH3:44])[CH3:43])[C@H:36]2[OH:45])[C@@:12]([O:47][CH3:48])([CH3:46])[CH2:11][C@@H:10]([CH3:49])/[C:7](=N\O)/[C@H:6]([CH3:50])[C@@H:5]([OH:51])[C@@:4]1([OH:53])[CH3:52].C(O)C.[OH-:57].[Na+]>O>[CH3:1][CH2:2][C@H:3]1[O:19][C:17](=[O:18])[C@H:16]([CH3:20])[C@@H:15]([O:21][C@@H:22]2[O:27][C@@H:26]([CH3:28])[C@H:25]([OH:29])[C@@:24]([O:31][CH3:32])([CH3:30])[CH2:23]2)[C@H:14]([CH3:33])[C@@H:13]([O:34][C@@H:35]2[O:40][C@H:39]([CH3:41])[CH2:38][C@H:37]([N:42]([CH3:43])[CH3:44])[C@H:36]2[OH:45])[C@@:12]([O:47][CH3:48])([CH3:46])[CH2:11][C@@H:10]([CH3:49])[C:7](=[O:57])[C@H:6]([CH3:50])[C@@H:5]([OH:51])[C@@:4]1([OH:53])[CH3:52]

参加物

5

反応物 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 9962216Clarithromycin 9-Oxime

生成物 1

HCID 84029Clarithromycin

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

In the present method, acid is added to the mixture of protected silylated clarithromycin oxime, ethanol, water and deoximating agent and the mixture is heated at reflux (about 80° C.) Heating is then continued and the suspension is stirred for an amount of time sufficient to finish the reaction. The mixture is then cooled to about 20° C. and sodium hydroxide solution having a concentration of from about 20% to about 47%, preferably 47%, is added at this temperature until the pH of the reaction mixture reaches about 10 to about 11, preferably about 10.2 to about 10.5. Crystalline clarithromycin is then isolated, preferably by filtration, with no further water addition. The obtained clarithromycin may subsequently be further purified and/or isolated and the crystalline form of clarithromycin may be altered to the desired form (such as crystal form 0, I, II, or IV) for use.

後処理

  1. temperaturethe mixture is heated
  2. temperatureHeating
  3. customthe reaction
  4. temperatureThe mixture is then cooled to about 20° C.
  5. additionis added at this temperature until the pH of the reaction mixture

出典と根拠

ORDレコード
ord-5b04e74c6ce249a49642d1e574b8f82d
出典データセット
uspto-grants-2006_09
特許番号
US07101858B2

関連ノート

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