Ammonia → N-Demethylerythromycin A

HRID 36843

反応式

HRID 36843 の反応式
[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]

参加物

7

反応物 4

HCID 222AmmoniaHCID 807IodineHCID 12560ErythromycinHCID 517045Sodium Acetate

生成物 1

HCID 10010092N-Demethylerythromycin A収率 40.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 22242641Methanol--water (1/1)溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a5e8b30eff0043a4993d87753dbbf392
出典データセット
uspto-grants-1995_05
特許番号
US05418224

関連ノート

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