Methyl iodide → HCID 54071906, compound

HRID 1287577Notes

Reaction equation

HRID 1287577 reaction equation
[C:1]([NH:4][C@H:5]1[C@@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:11]([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:10][C@@H:7]([O:8][CH3:9])[C@@H:6]1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:40]I>CN(C=O)C>[CH3:40][N:4]([C@H:5]1[C@@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:11]([CH2:21][O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:10][C@@H:7]([O:8][CH3:9])[C@@H:6]1[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53774444HCID 53774444, compound

Product 1

HCID 54071906HCID 54071906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve methyl 3-acetamido-3-deoxy-2,4,6-tri-O-benzyl-β-D-galactopyranoside (5.05 g.) in dry DMF (100 ml.). With stirring in an atomsphere of dry nitrogen add 0.25 g. of sodium hydride and allow the mixture to stir for 1 hour. Add methyl iodide (2.0 g.) and continue stirring at room temperature for 16 hours. Evaporate the mixture in vacuo to ca 10 ml. then dilute with chloroform. Cautiously add water and shake, separate the layers and re-extract the chloroform layer 3 times with water. Dry the chloroform solution and evaporate to 50 ml. Add hexane to precipitate the title product of this example. Yield ca 4.7 g.

Workup

  1. additionadd 0.25 g
  2. stirringto stir for 1 hour
  3. customEvaporate the mixture in vacuo to ca 10 ml
  4. additionthen dilute with chloroform
  5. customseparate the layers
  6. extractionre-extract the chloroform layer 3 times with water
  7. dry with materialDry the chloroform solution
  8. customevaporate to 50 ml
  9. customAdd hexane to precipitate the title product of this example

Sources & evidence

ORD record
ord-0743f63855454047bf3ad2a9e50515a7
Source dataset
uspto-grants-1976_10
Patent number
US03985727

Reaction notes

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