Triethylamine → n-Galactosylgeranamide

HRID 1786641

反応式

HRID 1786641 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

HCID 67133929n-Galactosylgeranamide収率 46%

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 14798Sodium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-281f019ab44e493bac9d647da6402ad8
出典データセット
uspto-grants-2009_03
特許番号
US07507765B2

関連ノート

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