Acetic Acid → HCID 22803037, compound

HRID 1448532Notes

Reaction equation

HRID 1448532 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-b294307eaf164633843f9ba50f566439
Source dataset
uspto-grants-1979_12
Patent number
US04180655

Reaction notes

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