Citric Acid → 6,7-Bis(palmitoyloxy)-4-thiaheptanoic acid p-methoxybenzyl ester

HRID 1720787Notes

Reaction equation

HRID 1720787 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9](=[O:18])[CH2:10][CH2:11][S:12][CH2:13][CH:14]([OH:17])[CH2:15][OH:16])=[CH:5][CH:4]=1.[C:21](Cl)(=[O:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].CN([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44]N=1)C.[C:48](O)(=O)[CH2:49][C:50]([CH2:55][C:56]([OH:58])=O)(C(O)=O)O>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:18])[CH2:10][CH2:11][S:12][CH2:13][CH:14]([O:17][C:56](=[O:58])[CH2:55][CH2:50][CH2:49][CH2:48][CH2:42][CH2:47][CH2:46][CH2:45][CH2:44][CH2:19][CH2:20][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:15][O:16][C:21](=[O:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8206Palmitoyl chlorideHCID 218852-DimethylaminopyridineHCID 107093566,7-Dihydroxy-4-thiaheptanoic acid p-methoxybenzyl ester

Product 1

HCID 106052466,7-Bis(palmitoyloxy)-4-thiaheptanoic acid p-methoxybenzyl esterYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 6,7-dihydroxy-4-thiaheptanoic acid p-methoxybenzyl ester as obtained in Reference Example 2 (1.99 g) in methylene chloride (26 ml), triethylamine (4.6 ml), palmitoyl chloride (6.00 g) and dimethylaminopyridine (5 mg) were added at 0° C., followed by stirring at room temperature for 24 hours. After addition of 5% citric acid, the reaction mixture was extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was recrystallized (methanol-hexane) to yield the title compound (2.30 g, yield 45%) as a white powder.

Workup

  1. additionwere added at 0° C.
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washThe extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was recrystallized (methanol-hexane)

Sources & evidence

ORD record
ord-ebfeb13aa0c84d55a95dd7ab97ee6385
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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