Iodoethane → HCID 70478347, compound

HRID 370592Notes

Reaction equation

HRID 370592 reaction equation
[C:1]([NH:4][C@@H:5]1[C@H:12]([OH:13])[C@H:11]([CH3:14])[O:10][C@H:7]([O:8][CH3:9])[CH2:6]1)(=[O:3])[CH3:2].[CH2:15](I)[CH3:16]>CN(C)C=O.[Ag]=O>[C:1]([NH:4][C@@H:5]1[C@H:12]([O:13][CH2:15][CH3:16])[C@H:11]([CH3:14])[O:10][C@H:7]([O:8][CH3:9])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 70478457HCID 70478457, compound

Product 1

HCID 70478347HCID 70478347, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

5.0 g of methyl 3-acetamido-2,3,6-trideoxy-β-L-lyxohexopyranoside were heated at 45° C. in the dark in a mixture of 25 ml of ethyl iodide and 20 ml of dimethylformamide containing 10 g of silver oxide. After 17 hours, the mixture was filtered through Celite and the filtrate was evaporated. The gum obtained was purified by column chromatography to give 3.4 g of methyl 3-acetamido-2,3,6-trideoxy-4-O-ethyl-β-L-lyxohexopyranoside in the form of colourless crystals of melting point 199°-200° C.; [α]D20 =-75.0° (c=0.5% in methanol).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. customthe filtrate was evaporated
  3. customThe gum obtained
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f3ce7cf526a644f590f46b90c8a49f6e
Source dataset
uspto-grants-1985_07
Patent number
US04526960

Reaction notes

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