Reaction #1552037

ord-49af15b57400451182352f8dced080b7

Reaction equation

CCCCCCCCCCCCCCCC(=O)Cl
palmitoyl chloride
O=C1CCC(=O)N1O
N-hydroxysuccinimide
CCN(CC)CC
triethylamine
CCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
N-palmitoyloxy-Succinimide

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    WashAfter washed with 500 mL of water three times
  2. 2
    Dryingthe resultant solution was dried over magnesium sulfate
  3. 3
    Concentrationwas then concentrated under reduced pressure
  4. 4
    Otherto obtain 260.3 g (quant) of a colorless solid

Procedure

To a solution of 165 mL (0.544 mol) of palmitoyl chloride in 1 L of chloroform while cooled with ice with stirring, 69.8 g (0.598 mol) of N-hydroxysuccinimide was gradually added, and 83.1 mL (0.598 mol) of triethylamine was added dropwise thereto over 30 minutes. The resultant solution was stirred for 30 minutes while cooled with ice and for another 7 hours during which the resultant solution gradually reached room temperature. After washed with 500 mL of water three times, the resultant solution was dried over magnesium sulfate and was then concentrated under reduced pressure to obtain 260.3 g (quant) of a colorless solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08999300B2uspto-grants-2015_04