Ammonium → 2-Amino-5-[glycyl(methyl)amino]-3,4,6-trihydroxycyclohexyl 2,6-diamino-2,3,4,6,7-pentadeoxyheptopyranoside

HRID 1733545Notes

Reaction equation

HRID 1733545 reaction equation
[CH3:1][CH:2]([NH2:28])[C@H:3]1[O:8][C@H:7]([O:9][C@H:10]2[C@H:15]([OH:16])[C@H:14]([N:17]([C:19]([CH2:21][NH2:22])=[O:20])[CH3:18])[C@@H:13]([O:23]C)[C@@H:12]([OH:25])[C@@H:11]2[NH2:26])[C@H:6]([NH2:27])[CH2:5][CH2:4]1.OS(O)(=O)=O.OS(O)(=O)=O.[NH4+]>I.O>[CH3:1][CH:2]([NH2:28])[CH:3]1[O:8][CH:7]([O:9][CH:10]2[CH:15]([OH:16])[CH:14]([N:17]([C:19]([CH2:21][NH2:22])=[O:20])[CH3:18])[CH:13]([OH:23])[CH:12]([OH:25])[CH:11]2[NH2:26])[CH:6]([NH2:27])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 223AmmoniumHCID 51565Sulfuric acid--2-amino-5-[glycyl(methyl)amino]-3,6-dihydroxy-4-methoxycyclohexyl 2,6-diamino-2,3,4,6,7-pentadeoxyheptopyranoside (2/1)

Product 1

HCID 1589272-Amino-5-[glycyl(methyl)amino]-3,4,6-trihydroxycyclohexyl 2,6-diamino-2,3,4,6,7-pentadeoxyheptopyranosideYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24841Hydrogen iodideSolvent

Conditions

Temperature
62 °C

Procedure

Fortimicin A sulfate (1.48 g, 2.46 mmole) was dissolved in 160 ml of 48% hydriodic acid at room temperature. The solution was stirred and the temperature gradually raised to 62° C. Stirring was continued at 62° C. for 20 hours. The solution was diluted with 160 ml of water and passed through a 1.5 l. column of "Amberlite" lRC-50 in the ammonium form. The column was washed with water and eluted with an ammonium hydroxide gradient as described in Example 1 resulting in the recovery of 3-O-demethylfortimicin A in 25% yield.

Workup

  1. stirringStirring
  2. washThe column was washed with water
  3. washeluted with an ammonium hydroxide gradient

Sources & evidence

ORD record
ord-7a271ecbd7f9478e9867cd6ce9b9bd30
Source dataset
uspto-grants-1980_12
Patent number
US04242503

Reaction notes

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