Palmitoyl chloride → HCID 54545161, compound

HRID 2255519Notes

Reaction equation

HRID 2255519 reaction equation
S(O)(=O)(=O)C.[CH2:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15](=[O:28])[C:16]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([Br:26])[C:17]=1O)[CH3:7].[C:29](Cl)(=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>FC(F)(F)C(O)=O>[CH2:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15](=[O:28])[C:16]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([Br:26])[C:17]=1[C:29](=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH3:7]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 14668292HCID 14668292, compound

Product 1

HCID 54545161HCID 54545161, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-bromo-2-hydroxy-5,6-dimethoxybenzamide mesylate (0.48 g, 1 mmol) in 10 ml of trifluoroacetic acid was added palmitoyl chloride (0.55 ml, 2 mmol). The reaction mixture was stirred at ambient temperature over molecular sieves for 20 h. After evaporation of the solvent in vacuo ether was added to the residue and filtered. The filtrate was washed several times with a saturated KHCO3 solution and dried (MgSO4). After evaporation of the solvent in vacuo the resulting oil crystallized on cooling. Yield 0.42 g (67%). M.p. 46°-48° C. Rf value is 0.21 for title compound and 0.32 for starting compound (SiO2, TLC-plates, 20% MeOH in i-Pr2O as eluent).

Workup

  1. customAfter evaporation of the solvent in vacuo ether
  2. additionwas added to the residue
  3. filtrationfiltered
  4. washThe filtrate was washed several times with a saturated KHCO3 solution
  5. dry with materialdried (MgSO4)
  6. customAfter evaporation of the solvent in vacuo the resulting oil
  7. customcrystallized
  8. temperatureon cooling

Sources & evidence

ORD record
ord-2cf5cd173bc548ca8d16607a6fb2a925
Source dataset
uspto-grants-1993_08
Patent number
US05240957

Reaction notes

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