Myristoyl chloride → N-[3(R,S)-Tetradecanoyloxytetradecanoyloxy]succinimide

HRID 255473

Reaction equation

HRID 255473 reaction equation
[OH:1][CH:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][C:4]([O:6][N:7]1[C:11](=[O:12])[CH2:10][CH2:9][C:8]1=[O:13])=[O:5].[C:25](Cl)(=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>N1C=CC=CC=1>[C:25]([O:1][CH:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][C:4]([O:6][N:7]1[C:8](=[O:13])[CH2:9][CH2:10][C:11]1=[O:12])=[O:5])(=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 66986Myristoyl chlorideHCID 13577455N-[3(R,S)-hydroxytetradecanoyloxy]succinimide

Product 1

HCID 13577457N-[3(R,S)-Tetradecanoyloxytetradecanoyloxy]succinimide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5.6 g of N-[3(R,S)-hydroxytetradecanoyloxy]succinimide in 150 ml pyridine cooled to 0° are added 4.9 g of tetradecanoylchloride and the reaction mixture maintained at 4° for 12 hours. Excess reagent is destroyed with water, the mixture concentrated by evaporation and the residue chromatographed over silica gel (toluene/ethylacetate=95/5) to obtained the title compound as a syrup.

Workup

  1. temperaturethe reaction mixture maintained at 4° for 12 hours
  2. customExcess reagent is destroyed with water
  3. concentrationthe mixture concentrated by evaporation
  4. customthe residue chromatographed over silica gel (toluene/ethylacetate=95/5)

Sources & evidence

ORD record
ord-e4f40f97f1e24bfd9a0aa2dbc2fa56c5
Source dataset
uspto-grants-1987_10
Patent number
US04698331

Linked notes

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