Water → 71628-96-1

HRID 35726Notes

Reaction equation

HRID 35726 reaction equation
C[C@@H]1O[C@@H:6]([O:8][C@@H:9]2[C:14]3[C:15]([OH:43])=[C:16]4[C:27](=[O:28])[C:26]5[C:21](=[C:22]6[O:35][C@@H:34]7[O:36][C@@:30]([CH3:42])([C@H:31]([OH:41])[C@@H:32]([N:38]([CH3:40])[CH3:39])[C@@H:33]7[OH:37])[C:23]6=[CH:24][C:25]=5[OH:29])[C:19](=[O:20])[C:17]4=[CH:18][C:13]=3[CH2:12][C@:11]([OH:45])([CH3:44])[CH2:10]2)[C@H](OC)[C@@](OC)(C)[C@H]1OC.FC(F)(F)C(O)=O.C[O-].[Na+].O>CO.C(Cl)(Cl)Cl>[CH3:44][C@@:11]1([OH:45])[CH2:12][C:13]2[CH:18]=[C:17]3[C:19](=[O:20])[C:21]4[C:26](=[C:25]([OH:29])[CH:24]=[C:23]5[C:30]6([CH3:42])[O:36][CH:34]([C@@H:33]([OH:37])[C@H:32]([N:38]([CH3:39])[CH3:40])[C@H:31]6[OH:41])[O:35][C:22]5=4)[C:27](=[O:28])[C:16]3=[C:15]([OH:43])[C:14]=2[C@@H:9]([O:8][CH3:6])[CH2:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 152474DisnogamycinHCID 10942334Sodium Methoxide2×

Product 1

HCID 32069771628-96-1

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A Solution of 1 g. of nogamycin in 20 ml. of trifluoroacetic acid is cooled in an ice bath and stirred for 5 hours. Stirring is continued while a solution of sodium methoxide in methanol is added dropwise until the reaction mixture turns purple. One hundred ml. of water is added, the pH is adjusted to 7.0 with additional sodium methoxide, and the mixture is extracted with three 100-ml. portions of methylene chloride. The combined extracts are evaporated to dryness under reduced pressure, wt. 1.004 g. A mixture of 0.5 g. of residue, 15 ml. of 0.1 M glucuronic acid, 10 ml. water, and 10 ml. of methanol is stirred for 15 minutes and filtered. The filtrate is neutralized (pH 7.0) with 1 N sodium hydroxide and stirred while maintaining at pH 7. After about 30 minutes the precipitate is collected by filtration, yield 211 mg. of con 7-0-methylnogarol. TLC in chloroform-methanol-water (78:20:2) indicates the material is homogeneous and identical with the same material prepared by methanolysis: [α]D 897° (c 0.1525, CHCl3); 13C NMR identical with that of previously prepared material; mass spectrum m/e 541.

Workup

  1. stirringStirring
  2. additionis added dropwise until the reaction mixture
  3. extractionthe mixture is extracted with three 100-ml
  4. customThe combined extracts are evaporated to dryness under reduced pressure, wt. 1.004 g
  5. additionA mixture of 0.5 g
  6. stirringof methanol is stirred for 15 minutes
  7. filtrationfiltered
  8. stirringstirred
  9. temperaturewhile maintaining at pH 7
  10. filtrationAfter about 30 minutes the precipitate is collected by filtration, yield 211 mg
  11. customprepared by methanolysis

Sources & evidence

ORD record
ord-bbfebbad062b4e39a2d6c075d4d108dd
Source dataset
uspto-grants-1988_08
Patent number
US04767847

Reaction notes

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