Formic Acid → Azithromycin

HRID 24271

반응식

HRID 24271 반응식
[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[CH2:8][NH:7][C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50].[CH:52](O)=O.C=O.[OH-].[Na+]>C(#N)C>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[CH2:8][N:7]([CH3:52])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 98106019-Deoxo-9a-aza-9a-homoerythromycin A

생성물 1

HCID 447043Azithromycin

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

9-Deoxo-9a-aza-9a-homoerythromycin A (73.5 g —0.1 mole) was dissolved in 250 ml acetonitrile. To this solution, formic acid (19 ml, 0.5 mole) followed by formaldehyde (37%, 20 ml, 0.25 mole) were added and refluxed for 24 hours. The pH of the reaction mixture was adjusted with alkali (NaOH solution) to 10.5 and filtered to remove particles. To the filtered acetonitrile solution, an equal volume of water was added to precipitate Azithromycin monohydrate as cube shaped crystals. The crystals were filtered and dried under vacuum at 50° C. to give 65 g of Azithromycin monohydrate having water content of 5% (water content measured by the Karl Fischer titration method). This sample of Azithromycin monohydrate crystals has a characteristic solid state (KBr pellet) IR spectrum (FIG. 1) and a characteristic X-ray diffraction pattern (FIG. 2).

후처리

  1. additionwere added
  2. temperaturerefluxed for 24 hours
  3. filtrationfiltered
  4. customto remove particles
  5. additionTo the filtered acetonitrile solution, an equal volume of water was added
  6. customto precipitate Azithromycin monohydrate as cube
  7. filtrationThe crystals were filtered
  8. customdried under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-388a27038ac94207a913ef159e6017a5
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855813B2

연결된 노트

불러오는 중…