HCID 22803039, compound → HCID 22803036, compound

HRID 2083784Notes

Reaction equation

HRID 2083784 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-9a69521953a54f34a59eeae5998deb70
Source dataset
uspto-grants-1978_04
Patent number
US04086415

Reaction notes

Loading…