Dimethylformamide → N-Methyl-D-glucamine
Reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11]O)[OH:10])[OH:8])[OH:6])[OH:4].[CH3:13][N:14](C)C=O>>[CH3:13][NH:14][CH2:11][C@@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[OH:6])[OH:8])[OH:10]Participants
Procedure
20 g of polifungin and 6 g of glucose were dissolved in 100 ml of dimethyl formamide and then the further procedure was carried out as in the Example IV till the moment of washing with water of precipitated N-glycosyl polifungin. The washed precipitate was suspended in 1200 ml of methanol of the temperature of 50° C., then was stirred and 7 g of N-methylglucamine, dissolved in 70 ml of water, were added. After dissolving the solution was filtered, 800 ml of n-amyl alcohol were added and the whole was concentrated under the reduced pressure at the temperature of 40° C. till the moment of removal of methanol and water. The resulting precipitate was filtered and washed with acetone. The precipitate was dried at a room temperature under the reduced pressure. 16.3 g of N-methylglucamine salt of N-glycosyl polifungin of biological activity of 1980 U/mg, E1 cm1% =572 at 304 nm were obtained. Original antibiotic exhibited E1 cm1% =720 at 304 nm.
Workup
- washof washing with water of precipitated N-glycosyl polifungin
- customwas suspended in 1200 ml of methanol of the temperature of 50° C.
- dissolution7 g of N-methylglucamine, dissolved in 70 ml of water
- additionwere added
- dissolutionAfter dissolving the solution
- filtrationwas filtered
- addition800 ml of n-amyl alcohol were added
- concentrationthe whole was concentrated under the reduced pressure at the temperature of 40° C. till the moment of removal of methanol and water
- filtrationThe resulting precipitate was filtered
- washwashed with acetone
- customThe precipitate was dried at a room temperature under the reduced pressure
Sources & evidence
- ORD record
- ord-c34505746dae41ab8db5c59118e13725
- Source dataset
- uspto-grants-1980_03
- Patent number
- US04195172
Reaction notes
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