反応 #1528401

ord-127ea22c25e346dc8ff7c231b1553294

反応方程式

NCCS
2-aminoethanethiol
CCCCCCCCCCCCCC(=O)Cl
Myristoyl chloride
c1ccncc1
pyridine
O=C1CCC(=O)N1O
N-hydroxysuccinimide
CCCCCCCCCCCCCC(=O)NCCS
N-(Myristoyl) 2-Aminoethane Thiol

溶媒

反応条件

温度
23°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他to react for 6 h at ambient temperature
  2. 2
    workup.WAITfollowed by 3 days at 4° C
  3. 3
    workup.STIRRINGstirred for 1 h at ambient and
  4. 4
    ろ過filtered
  5. 5
    洗浄washing with cold water
  6. 6
    workup.DISSOLUTIONThe white solid was dissolved in dimethylsulphoxide
  7. 7
    その他reprecipitated with water
  8. 8
    乾燥vacuum dried over phosphorous pentoxide

実験手順

Myristoyl chloride (1.0 mmol) was added with vigorous string to ice-cooled dry pyridine (1.0 ml), and followed immediately by N-hydroxysuccinimide (1.5 mmol). The mixture was stirred for 4 h at ambient temperature (˜23° C.). 2-aminoethanethiol free base (1.1 mmol) was added as solid to the mixture and allowed to react for 6 h at ambient temperature, followed by 3 days at 4° C. The product was treated with water (5 ml), stirred for 1 h at ambient and filtered, washing with cold water. The white solid was dissolved in dimethylsulphoxide and reprecipitated with water and then vacuum dried over phosphorous pentoxide. The final yield was 0.21 g (˜70%). Thiol titration using Ellman's reagent indicated that the product contained ˜45% free thiol.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07655617B2uspto-grants-2010_02