Potassium Hydroxide → HCID 131718681, compound

HRID 2226987Notes

Reaction equation

HRID 2226987 reaction equation
[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]([O:46]C)([CH3:45])[CH2:10][C@@H:9]([CH3:48])[C:7](=[O:8])[C@H:6]([CH3:49])[C@@H:5]([OH:50])[C@@:4]1([OH:52])[CH3:51].[OH-].[K+].Cl[C:56]([O:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH3:69])=[O:57]>O1CCCC1>[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]([CH3:42])[CH3:43])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:48])[C:7](=[O:8])[C@H:6]([CH3:49])[C@@H:5]([OH:50])[C@@:4]1([OH:52])[CH3:51].[CH2:68]([O:67][CH2:66][CH2:65][O:64][CH2:63][CH2:62][O:61][CH2:60][CH2:59][O:58][C:56](=[O:8])[O-:57])[CH3:69]

Participants

6

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 84029ClarithromycinHCID 189641252-[2-(2-Ethoxyethoxy)ethoxy]ethyl carbonochloridate2×

Product 2

HCID 12560ErythromycinHCID 131718681HCID 131718681, compoundYield 598.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-O-methylerythromycin A (10 g) in tetrahydrofuran (50 ml ), were added 95 % potassium hydroxide powder (0.87 g ) and 2 - [2 - (2 -ethoxyethoxy ) ethoxy ]ethyl chloroformate (3.60 g) under ice-cooling. After stirring for 3 hours, 95% potassium hydroxide powder (0.24 g ) and 2- [2-(2 -ethoxyethoxy ) ethoxy ]ethyl chloroformate (0.98 g ) were further added thereto and the mixture was stirred for additional 2 days. The post treatment was performed by the same method as the one described in Example 7. The crude product thus obtained was purified by silica gel column chromatography (elution solvent; acetone : n-hexane =7 : 13 - 2 : 3) and then crystallized from chloroform/n-hexane. Thus 6-0-methylerythromycin A 2 '- {2- [2- (2-ethoxyethoxy ) ethoxy]ethyl}carbonate (8.85 g) was obtained as a white powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for additional 2 days
  3. customThe crude product thus obtained
  4. customwas purified by silica gel column chromatography (elution solvent; acetone : n-hexane =7 : 13 - 2 : 3)
  5. customcrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-5cc3e8eaab8c41e4b3d99d11b62d7aca
Source dataset
uspto-grants-1994_09
Patent number
US05350839

Reaction notes

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