Triethylamine → n-Galactosylgeranamide

HRID 1987709Notes

Reaction equation

HRID 1987709 reaction equation
[C:1]([OH:12])(=O)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C([N:15]([CH2:18][CH3:19])CC)C.ClC(OCC(C)C)=[O:22].Cl.OC1[O:38][C@H:37]([CH2:39][OH:40])[C@H:35]([OH:36])[C@H:33]([OH:34])[C@H]1N>O.[OH-].[Na+].CC(C)=O.C1COCC1>[CH:18]1([NH:15][C:1](=[O:12])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])[O:38][C@H:37]([CH2:39][OH:40])[C@H:35]([OH:36])[C@H:33]([OH:34])[C@H:19]1[OH:22]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 2723866D-(+)-Galactosamine hydrochlorideHCID 5275520Geranic acid

Product 1

HCID 67133929n-GalactosylgeranamideYield 46%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a THF (20 ml) solution containing geranic acid (0.84 g, 5 mmols), triethylamine (0.51 g, 5 mmols) was added and cooled to 0° C., into which a THF (5 ml) solution containing isobutyl chloroformate (0.68 g, 5 mmols) was added dropwise, followed by 30 minutes' stirring at 0° C. Then galactosamine hydrochloride (1.08 g, 5 mmols) was dissolved in 10 ml of water, to which 5 ml of 1N sodium hydroxide was further added, and the solution was added to the reaction mixture all at a time. After the following stirring for an hour at 0° C. and for further 4 hours at room temperature, the reaction mixture was condensed under reduced pressure. To the residue 150 ml of acetone was added and precipitated sodium chloride was filtered off. The filtrate was condensed once again and the residue was separated on silica gel column chromatography. Consequently the product was obtained from the hexane-ethanol (2:1) distillate as a viscous oily substance, to which a minor amount of ether was added to crystallize the product. Through subsequent suction filtration, 0.754 g of the title compound was obtained. The yield was 46%, and the melting point was 85-87° C.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. additionwas further added
  4. additionthe solution was added to the reaction mixture all at a time
  5. stirringAfter the following stirring for an hour at 0° C. and for further 4 hours at room temperature
  6. customcondensed under reduced pressure
  7. customprecipitated sodium chloride
  8. filtrationwas filtered off
  9. customcondensed once again
  10. customthe residue was separated on silica gel column chromatography
  11. customConsequently the product was obtained from the hexane-ethanol (2:1) distillate as a viscous oily substance, to which a minor amount of ether
  12. additionwas added
  13. customto crystallize the product
  14. filtrationThrough subsequent suction filtration

Sources & evidence

ORD record
ord-abbd88faf35442bd829129d321e41ba6
Source dataset
uspto-grants-2009_06
Patent number
US07553820B2

Reaction notes

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