Ethanol → Clarithromycin

HRID 2211583

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HRID 2211583 반응식
[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]

참가 물질

5

반응물 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 9962216Clarithromycin 9-Oxime

생성물 1

HCID 84029Clarithromycin

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b04e74c6ce249a49642d1e574b8f82d
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101858B2

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