Acetic Acid → HCID 22803037, compound

HRID 2083785Notes

Reaction equation

HRID 2083785 reaction equation
[S:1]([O:5][CH2:6][C@H:7]1[O:14][C@@H:11]([O:12][CH3:13])[C@H:10]([NH:15][C:16]([NH:18][CH3:19])=[O:17])[C@@H:9]([OH:20])[C@@H:8]1[OH:21])([CH3:4])(=[O:3])=[O:2].C(O)(=O)C.[N:26]([O-])=[O:27].[Na+]>O>[S:1]([O:5][CH2:6][C@H:7]1[O:14][C@@H:11]([O:12][CH3:13])[C@H:10]([NH:15][C:16]([N:18]([CH3:19])[N:26]=[O:27])=[O:17])[C@@H:9]([OH:20])[C@@H:8]1[OH:21])([CH3:4])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 22803040HCID 22803040, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22803037HCID 22803037, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-deoxy-6-O-mesyl-2-(N'-methylureido)-β-D-glucopyranoside (400 mg) of the formula ##STR36## was dissolved in 50 ml of water, and the resulting aqueous solution was adjusted to pH 3 by addition of 2 ml of acetic acid. The acidified aqueous solution was admixed with 120 mg of sodium nitrite and the mixture was agitated at ambient temperature overnight to effect the nitrosation. The reaction mixture was treated with Amberlite IR-120 (H+ form) to remove the sodium ion therefrom. The reaction mixture was then evaporated under a reduced pressure at a temperature below 25° C. The residue was crystallized from ethanol to give 350 mg of the titled compound. mp. 131°-132° C (with decomposition). [α]D20 -14° (c 0.5, dimethylsulfoxide).

Workup

  1. additionThe reaction mixture was treated with Amberlite IR-120 (H+ form)
  2. customto remove the sodium ion
  3. customThe reaction mixture was then evaporated under a reduced pressure at a temperature below 25° C
  4. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-d2ff495e89c8478b9d9315aa16b15c64
Source dataset
uspto-grants-1978_04
Patent number
US04086415

Reaction notes

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