Ammonia → N-Demethylerythromycin A

HRID 36843

반응식

HRID 36843 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](C)[CH3:42])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50].C([O-])(=O)C.[Na+].II.N>CO.O.O>[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]([NH:41][CH3:42])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 807IodineHCID 12560ErythromycinHCID 517045Sodium Acetate

생성물 1

HCID 10010092N-Demethylerythromycin A수율 40.8%

시약·촉매·용매 2

HCID 962Water용매HCID 22242641Methanol--water (1/1)용매

실험 절차

5 g of erythromycin A and 4.7 g of sodium acetate (×3 H2O) were dissolved in 200 ml of an 8:2 methanol/water mixture. 1.75 g of iodine were added to the solution, and the reaction mixture was then irradiated with a quartz lamp at room temperature for 20 minutes. Subsequently, half the solvent was evaporated, and the remaining reaction mixture was poured into a mixture of 140 ml of water and 10 ml of ammonia. The reaction mixture was extracted three times with 20 ml portions of methyl t-butyl ether. The ether extract was separated and some of the ether was evaporated. The reaction product was then left to crystallize out and was recrystallized from acetone. 2 g of N-demethylerythromycin A were obtained.

후처리

  1. customthe reaction mixture was then irradiated with a quartz lamp at room temperature for 20 minutes
  2. customSubsequently, half the solvent was evaporated
  3. customthe remaining reaction mixture
  4. extractionThe reaction mixture was extracted three times with 20 ml portions of methyl t-butyl ether
  5. extractionThe ether extract
  6. customwas separated
  7. customsome of the ether was evaporated
  8. waitThe reaction product was then left
  9. customto crystallize out
  10. customwas recrystallized from acetone

출처 및 근거

ORD 기록
ord-a5e8b30eff0043a4993d87753dbbf392
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418224

연결된 노트

불러오는 중…