Ethanol → Rifaximin

HRID 1747726Notes

Reaction equation

HRID 1747726 reaction equation
O.C(O)C.[CH3:5][C@@H:6]1[C@H:40]([OH:41])[C@@H:39]([CH3:42])[C@@H:38]([OH:43])[C@@H:37]([CH3:44])[C@H:36]([O:45][C:46]([CH3:48])=[O:47])[C@H:35]([CH3:49])[C@@H:34]([O:50][CH3:51])[CH:33]=[CH:32][O:31][C@:28]2([CH3:52])[C:29](=[O:30])[C:18]3[C:19]([O:27]2)=[C:20]([CH3:26])[C:21]([OH:25])=[C:22]2[C:23](=[O:24])[C:14](=[CH:15][C:16]4(OC(=O)CO4)[C:17]=32)[NH:13][C:11](=[O:12])[C:10]([CH3:58])=[CH:9][CH:8]=[CH:7]1.[NH2:59][C:60]1[CH:65]=[C:64]([CH3:66])[CH:63]=[CH:62][N:61]=1>CC(C)=O>[CH3:66][C:64]1[CH:63]=[CH:62][N:61]2[C:15]3[C:14]4[NH:13][C:11](=[O:12])[C:10]([CH3:58])=[CH:9][CH:8]=[CH:7][C@H:6]([CH3:5])[C@H:40]([OH:41])[C@@H:39]([CH3:42])[C@@H:38]([OH:43])[C@@H:37]([CH3:44])[C@H:36]([O:45][C:46]([CH3:48])=[O:47])[C@H:35]([CH3:49])[C@@H:34]([O:50][CH3:51])[CH:33]=[CH:32][O:31][C@:28]5([CH3:52])[C:29](=[O:30])[C:18]6=[C:19]([O:27]5)[C:20]([CH3:26])=[C:21]([OH:25])[C:22](=[C:17]6[C:16]=3[N:59]=[C:60]2[CH:65]=1)[C:23]=4[OH:24]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 15332-Amino-4-methylpyridineHCID 5280468Rifamycin, 4-O-(carboxymethyl)-1-deoxy-1,4-dihydro-4-hydroxy-1-oxo-, gamma-lactone

Product 1

HCID 6436173Rifaximin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In flask equipped with a mechanic stirrer, 200 ml of demineralized water, 150 ml of ethyl alcohol, 50 ml of acetone, 100 g of Rifamycin O and 43.3 g of 2-amino-4-methylpyridine are loaded in succession at room temperature. After loading, the mixture is kept under stirring at room temperature for 24 hours, then is cooled to 10° C. for 60 minutes. Then the precipitate is filtered and washed by means of a mixture of 100 ml of demineralized water and 100 ml of ethyl alcohol and at least with two washing of 100 ml of demineralized water. The product is dried under vacuum at 70° C. until the water content is between 2.0 and 4.5%.

Workup

  1. customIn flask equipped with a mechanic stirrer
  2. customare loaded in succession at room temperature
  3. temperatureis cooled to 10° C. for 60 minutes
  4. filtrationThen the precipitate is filtered
  5. washwashed by means of a mixture of 100 ml of demineralized water and 100 ml of ethyl alcohol
  6. washat least with two washing of 100 ml of demineralized water
  7. dry with materialThe product is dried under vacuum at 70° C. until the water content

Sources & evidence

ORD record
ord-4c9e5e709a674d60a49a7343af7aa127
Source dataset
uspto-grants-2015_10
Patent number
US09150590B2

Reaction notes

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