HCID 22803039, compound → HCID 22803036, compound

HRID 1448531Notes

Reaction equation

HRID 1448531 reaction equation
[CH3:1][NH:2][C:3](=[O:16])[NH:4][C@@H:5]1[C@@H:12]([OH:13])[C@H:11]([OH:14])[C@@H:10]([CH3:15])[O:9][C@H:6]1[O:7][CH3:8].[N:17]([O-])=[O:18].[Na+]>C(O)(=O)C.O>[CH3:1][N:2]([N:17]=[O:18])[C:3](=[O:16])[NH:4][C@@H:5]1[C@@H:12]([OH:13])[C@H:11]([OH:14])[C@@H:10]([CH3:15])[O:9][C@H:6]1[O:7][CH3:8]

Participants

5

Reactant 2

HCID 22803039HCID 22803039, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22803036HCID 22803036, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Methyl 2,6-dideoxy-2-(N'-methyl-ureido)-β-D-glucopyranoside (124 mg) of the formula: ##STR35## was dissolved in a mixture of 0.5 ml of glacial acetic acid and 2.5 ml of water, and the resulting solution was admixed with 55 mg of sodium nitrite at ambient temperature and under agitation to effect the nitrosation. The reaction mixture so obtained was then allowed to stand overnight in a refrigerator, so that a crystalline product was deposited. This crystalline product was collected by filtration and then washed with ethanol, affording 80 mg of methyl 2,6-dideoxy-2-(N'-methyl-N'-nitroso-ureido)-β-D-glucopyranoside as the desired product. The mother liquor was then treated with Amberlite IR-120 (H+ form) to remove the sodium ion, and the mother liquor so treated was concentrated by distilling off the solvent under reduced pressure. Crystallization of the residue from ethanol gave 45 mg of the desired product as a second crop. Yield 125 mg (90%). [α]D28 -14° (c 0.52, H2O).

Workup

  1. customThe reaction mixture so obtained
  2. filtrationThis crystalline product was collected by filtration
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-8527bb0386f84ede852663ff01975824
Source dataset
uspto-grants-1979_12
Patent number
US04180655

Reaction notes

Loading…