Ethanol → Rifaximin

HRID 409628노트

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HRID 409628 반응식
[CH3:1][C@@H:2]1[C@H:36]([OH:37])[C@@H:35]([CH3:38])[C@@H:34]([OH:39])[C@@H:33]([CH3:40])[C@H:32]([O:41][C:42]([CH3:44])=[O:43])[C@H:31]([CH3:45])[C@@H:30]([O:46][CH3:47])[CH:29]=[CH:28][O:27][C@:24]2([CH3:48])[C:25](=[O:26])[C:14]3[C:15]([O:23]2)=[C:16]([CH3:22])[C:17]([OH:21])=[C:18]2[C:19](=[O:20])[C:10](=[CH:11][C:12]4(OC(=O)CO4)[C:13]=32)[NH:9][C:7](=[O:8])[C:6]([CH3:54])=[CH:5][CH:4]=[CH:3]1.C(O)C.[NH2:58][C:59]1[CH:64]=[C:63]([CH3:65])[CH:62]=[CH:61][N:60]=1.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>Cl.O>[CH3:65][C:63]1[CH:62]=[CH:61][N:60]2[C:11]3[C:10]4[NH:9][C:7](=[O:8])[C:6]([CH3:54])=[CH:5][CH:4]=[CH:3][C@H:2]([CH3:1])[C@H:36]([OH:37])[C@@H:35]([CH3:38])[C@@H:34]([OH:39])[C@@H:33]([CH3:40])[C@H:32]([O:41][C:42]([CH3:44])=[O:43])[C@H:31]([CH3:45])[C@@H:30]([O:46][CH3:47])[CH:29]=[CH:28][O:27][C@:24]5([CH3:48])[C:25](=[O:26])[C:14]6=[C:15]([O:23]5)[C:16]([CH3:22])=[C:17]([OH:21])[C:18](=[C:13]6[C:12]=3[N:58]=[C:59]2[CH:64]=1)[C:19]=4[OH:20]

참가 물질

7

반응물 4

HCID 702EthanolHCID 15332-Amino-4-methylpyridineHCID 5280468Rifamycin, 4-O-(carboxymethyl)-1-deoxy-1,4-dihydro-4-hydroxy-1-oxo-, gamma-lactoneHCID 54670067L-Ascorbic Acid

생성물 1

HCID 6436173Rifaximin

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매2회

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온도
27.5 °C

실험 절차

Rifamycin O (50 g) and 76 ml of ethanol were stirred in a RBF at 20-30° C., for 15 minutes, DM water (100 ml) and 21.5 g of 2-Amino-4-picoline were added and stirred for 15 minutes at 25-30° C. The reaction mass was heated to 47° C. and stirred for 4-5 hours. Reaction mass was cooled to 20° C. and a solution of 1.32 g of ascorbic acid in 10 ml of concentrated HCl and 7.1 ml of DM water was added into it in 30 minutes. The reaction mixture was stirred for 30 minutes at 20° C.; ˜8.75 ml of concentrated HCl was added into it to adjust the pH to 1.5-2.0 and further stirred. The crude was isolated by filtration, washed with 100 ml of 1:1 Ethanol and water mixture. The Crude was pulped with DM water until the pH of filtrate is neutral, dried for 10-12 hours at 70° C. until the moisture content was <5.0%.

후처리

  1. temperatureThe reaction mass was heated to 47° C.
  2. stirringstirred for 4-5 hours
  3. customReaction mass
  4. temperaturewas cooled to 20° C.
  5. stirringThe reaction mixture was stirred for 30 minutes at 20° C.
  6. stirringfurther stirred
  7. customThe crude was isolated by filtration
  8. washwashed with 100 ml of 1:1 Ethanol and water mixture
  9. customdried for 10-12 hours at 70° C. until the moisture content

출처 및 근거

ORD 기록
ord-abce733687f54a1f84d92fcdafb7159d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759513B2

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