Benzyl Bromide → HCID 53774444, compound

HRID 1287575Notes

Reaction equation

HRID 1287575 reaction equation
[C:1]([NH:4][C@H:5]1[C@@H:12]([OH:13])[C@@H:11]([CH2:14][OH:15])[O:10][C@@H:7]([O:8][CH3:9])[C@@H:6]1[OH:16])(=[O:3])[CH3:2].[O-2].[Ba+2].[OH-].[Ba+2].[OH-].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[C:1]([NH:4][C@H:5]1[C@@H:12]([O:13][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:11]([CH2:14][O:15][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:10][C@@H:7]([O:8][CH3:9])[C@@H:6]1[O:16][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 6093286Barium hydroxideHCID 9855530Barium Oxide Nanoparticle DispersionHCID 54002028HCID 54002028, compound

Product 1

HCID 53774444HCID 53774444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 15 g. of methyl 3-acetamido-3-deoxy-β-D-galactopyranoside in DMF (300 ml.). To the solution add barium oxide (111 g.) and barium hydroxide (51 g.) and cool to 0°. With rapid stirring add benzyl bromide (150 ml.) dropwise. Allow the mixture to stir for a further 4 hours at 0° and then 16 hours at room temperature. Dilute the reaction mixture with 750 ml. of chloroform and filter. Concentrate the filtrate at 60° in vacuo to a yellow syrup, and extract this syrup with 500 ml of ethyl acetate. Filter the extract and concentrate in vacuo to a residue. Dissolve the residue in chloroform (200 ml.), wash the solution with 3 × 100 ml. of water then dry the chloroform phase over MgSO4. Remove the MgSO4 by filtration, then add hexane to the filtrate till crystals appear. After standing to complete the crystallization, filter off the product and dry to obtain methyl 3-acetamido-3-deoxy-2,4,6-tri-O-benzyl-β-D-galactopyranoside, 29.53 g. m.p. 147°-151°, [α d26 +52.5°.

Workup

  1. dissolutionDissolve 15 g
  2. temperaturecool to 0°
  3. stirringAllow the mixture to stir for a further 4 hours at 0°
  4. custom16 hours
  5. customat room temperature
  6. additionDilute the reaction mixture with 750 ml
  7. filtrationof chloroform and filter
  8. concentrationConcentrate the filtrate at 60° in vacuo to a yellow syrup
  9. extractionextract this syrup with 500 ml of ethyl acetate
  10. filtrationFilter the
  11. extractionextract
  12. concentrationconcentrate in vacuo to a residue
  13. dissolutionDissolve the residue in chloroform (200 ml.)
  14. washwash the solution with 3 × 100 ml
  15. dry with materialof water then dry the chloroform phase over MgSO4
  16. customRemove the MgSO4
  17. filtrationby filtration
  18. customthe crystallization
  19. filtrationfilter off the product
  20. customdry

Sources & evidence

ORD record
ord-73c8b059c02b4d708239bc102f2b8dfc
Source dataset
uspto-grants-1976_10
Patent number
US03985727

Reaction notes

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