Reaction #1528401

Reaction equation

2-aminoethanethiol

Myristoyl chloride

pyridine

N-hydroxysuccinimide

→

N-(Myristoyl) 2-Aminoethane Thiol

Solvents

water

Conditions

Workup

1. 1
   Otherto 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
   Filtrationfiltered
5. 5
   Washwashing with cold water
6. 6
   workup.DISSOLUTIONThe white solid was dissolved in dimethylsulphoxide
7. 7
   Otherreprecipitated with water
8. 8
   Dryingvacuum dried over phosphorous pentoxide

Procedure

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.

Source