Methanol → O-Methylconcanamycin A

HRID 976028Notes

Reaction equation

HRID 976028 reaction equation
[CH3:1][CH2:2][C@@H:3]1[C@H:21]([OH:22])[C@H:20]([CH3:23])[CH:19]=[C:18]([CH3:24])[CH:17]=[C:16]([O:25][CH3:26])[C:14](=[O:15])[O:13][C@H:12]([C@H:27]([C@@H:29]([OH:56])[C@@H:30]([C@:32]2([OH:55])[O:37][C@H:36](/[CH:38]=[CH:39]/[CH3:40])[C@@H:35]([CH3:41])[C@H:34]([O:42][C@@H:43]3[O:48][C@H:47]([CH3:49])[C@@H:46]([O:50][C:51]([NH2:53])=[O:52])[C@H:45]([OH:54])[CH2:44]3)[CH2:33]2)[CH3:31])[CH3:28])[C@@H:11]([O:57][CH3:58])[CH:10]=[CH:9][CH:8]=[C:7]([CH3:59])[CH2:6][C@@H:5]([CH3:60])[C@@H:4]1[OH:61].P([O-])([O-])([O-])=O.[CH3:67]O>>[CH3:1][CH2:2][C@@H:3]1[C@H:21]([OH:22])[C@H:20]([CH3:23])[CH:19]=[C:18]([CH3:24])[CH:17]=[C:16]([O:25][CH3:26])[C:14](=[O:15])[O:13][C@H:12]([C@H:27]([C@@H:29]([OH:56])[C@@H:30]([C@:32]2([O:55][CH3:67])[O:37][C@H:36](/[CH:38]=[CH:39]/[CH3:40])[C@@H:35]([CH3:41])[C@H:34]([O:42][C@@H:43]3[O:48][C@H:47]([CH3:49])[C@@H:46]([O:50][C:51]([NH2:53])=[O:52])[C@H:45]([OH:54])[CH2:44]3)[CH2:33]2)[CH3:31])[CH3:28])[C@@H:11]([O:57][CH3:58])[CH:10]=[CH:9][CH:8]=[C:7]([CH3:59])[CH2:6][C@@H:5]([CH3:60])[C@@H:4]1[OH:61]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 1061PhosphateHCID 6438151Concanamycin A

Product 1

HCID 11061923O-Methylconcanamycin A

Procedure

In a thoroughly heated 50 ml flask, 800 mg (0.92 mmol) of concanamycin A are dissolved in 19 ml of dry MeOH. 15 mg of FeCl3 (0.09 mmol, 0.1 equiv.) in 1 ml of MeOH are then added and the mixture is stirred for 15 min at room temperature. After the addition of 20 ml of phosphate buffer (pH=7, Merck), the solution is transferred to a 250 ml flask and the organic solvent is carefully removed in vacuo. The remaining aqueous residue is extracted with CHCl3 and, after customary working-up, is filtered on silica gel (system D, 4×10) to yield the title compound. M.p. 141° C.

Workup

  1. customthe solution is transferred to a 250 ml flask
  2. customthe organic solvent is carefully removed in vacuo
  3. extractionThe remaining aqueous residue is extracted with CHCl3
  4. filtrationafter customary working-up, is filtered on silica gel (system D, 4×10)

Sources & evidence

ORD record
ord-a9da596cb2ee4e1f924ae355dddeae2e
Source dataset
uspto-grants-1997_03
Patent number
US05610178

Reaction notes

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