Palmitoyl chloride → HCID 53712566, compound

HRID 1720789Notes

Reaction equation

HRID 1720789 reaction equation
[C:1]([O:5][C:6](=[O:36])[CH2:7][CH2:8][S:9][CH2:10][CH:11]([OH:35])[CH2:12][O:13][C:14](=[O:34])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH3:4])([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.[C:46](Cl)(=[O:62])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61]>ClCCl>[C:1]([O:5][C:6](=[O:36])[CH2:7][CH2:8][S:9][CH2:10][CH:11]([O:35][C:46](=[O:62])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:12][O:13][C:14](=[O:34])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 218852-DimethylaminopyridineHCID 54117669HCID 54117669, compound

Product 1

HCID 53712566HCID 53712566, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-hydroxy-7-octadecylcarbamoyloxy-4-thiaheptanoic acid t-butyl ester as obtained in Reference Example 7 (2.98 g), dimethylaminopyridine (820 mg) and palmitoyl chloride (1.54 g) in dichloromethane (10 ml) was stirred at room temperature for 30 minutes, followed by solvent concentration under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1) to yield the title compound (3.425 g, yield 79%) as a colorless wax-like substance.

Workup

  1. concentrationfollowed by solvent concentration under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9329c77748fc403cba390fa9e55344ab
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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