Erythromycin → Flurithromycin

HRID 742175Notes

Reaction equation

HRID 742175 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]([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].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:62])(=O)=O)=CC=1>C(O)(=O)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]([CH3:42])[CH3:43])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@:9]([F:62])([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

Participants

4

Reactant 2

HCID 12560ErythromycinHCID 588007N-Fluorobenzenesulfonimide

Product 1

HCID 71260FlurithromycinYield 96.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Erythromycin A (5 g, 6.813 mmole) and N-fluorobenzenesulfonimide (2.2 g 6,813 mmole) were dissolved in glacial acetic acid (20 mL) at room temperature and stirred for 18 hours. The reaction was worked-up in the same manner as Example 1 to afford 4.96 g of crude flurithromycin. This material was recrystallized as described in Example 1 to yield 2.25 g (44% yield) of fluorithromycin. This example shows that reasonably good yields of flurithromycin may be obtained in the process of the invention without buffering.

Sources & evidence

ORD record
ord-46f94b72d2d443f3a3943e5e89a16f11
Source dataset
uspto-grants-1996_09
Patent number
US05552533

Reaction notes

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