Hydrochloric Acid → Rifamycin P

HRID 614223

Reaktionsgleichung

Reaktionsgleichung von HRID 614223
[CH3:1][C:2]1[C:7]2[O:8][C@:9]3([CH3:49])[O:12][CH:13]=[CH:14][C@H:15]([O:47][CH3:48])[C@@H:16]([CH3:46])[C@@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:18]([CH3:41])[C@H:19]([OH:40])[C@H:20]([CH3:39])[C@@H:21]([OH:38])[C@@H:22]([CH3:37])[CH:23]=[CH:24][CH:25]=[C:26]([CH3:36])[C:27](NC4C(=O)[C:4](=[C:5]([C:32](=O)C=4)[C:6]=2[C:10]3=[O:11])[C:3]=1[OH:50])=[O:28].Cl.CO[C:54](=[O:59])[C@H:55]([CH2:57][SH:58])[NH2:56].[CH2:60]([N:62](CC)CC)C>CO>[CH3:37][CH:22]1[CH:21]([OH:38])[CH:20]([CH3:39])[CH:19]([OH:40])[CH:18]([CH3:41])[CH:17]([O:42][C:43]([CH3:45])=[O:44])[CH:16]([CH3:46])[CH:15]([O:47][CH3:48])[CH:14]=[CH:13][O:12][C:9]2([CH3:49])[C:10](=[O:11])[C:6]3=[C:7]([O:8]2)[C:2]([CH3:1])=[C:3]([OH:50])[C:4]2=[C:5]3[C:32]3[N:62]=[CH:60][S:58][C:57]=3[C:55](=[C:54]2[OH:59])[NH:56][C:27](=[O:28])[C:26]([CH3:36])=[CH:25][CH:24]=[CH:23]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 29145L-Cysteine, methyl esterHCID 6436726Rifamycin S

Produkt 1

HCID 6441079Rifamycin P

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 7 g of rifamycin S in 200 ml of methanol a mixture was added containing 1.8 g of the hydrochloride of cysteine methyl ester and 1.53 g of triethylamine. The mixture was refluxed for 20 minutes and then 20 ml of a buffer pH 4.6 containing 2.2 g of dichlorodicyano-p-quinone was added. The mixture was allowed to stand at room temperature for 15 hours and then was treated as described in Example 1 to obtain the rifamycin P. Yield 2.8 g of the title product.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 20 minutes
  2. additionwas added
  3. additionwas treated

Quellen und Nachweise

ORD-Eintrag
ord-c2e65e398f994877bdf007f3ea7a3f38
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04144234

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