Water → 6,7-Bis(palmitoyloxy)-2-methyl-4-thiaheptanoic acid t-butyl ester

HRID 1720802Notes

Reaction equation

HRID 1720802 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH:7]([CH3:15])[CH2:8][S:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:33])[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][CH3:32].CN([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40]N=1)C.[OH2:44]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:16])[CH:7]([CH3:15])[CH2:8][S:9][CH2:10][CH:11]([O:14][C:40](=[O:44])[CH2:41][CH2:42][CH2:43][CH2:38][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH2:12][O:13][C:17](=[O:33])[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][CH3:32])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8206Palmitoyl chlorideHCID 218852-DimethylaminopyridineHCID 106344486,7-Dihydroxy-2-methyl-4-thiaheptanoic acid t-butyl ester

Product 1

HCID 105329566,7-Bis(palmitoyloxy)-2-methyl-4-thiaheptanoic acid t-butyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 6,7-dihydroxy-2-methyl-4-thiaheptanoic acid t-butyl ester as obtained in Reference Example 40 (500 mg) in chloroform (30 ml), triethylamine (5.6 ml), palmitoyl chloride (5.50 g) and dimethylaminopyridine (5 mg) were added, followed by stirring at room temperature for 48 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with a 5% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to yield the title compound (1.33 g, yield 91%) as a colorless oily substance.

Workup

  1. additionwere added
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with a 5% aqueous solution of citric acid
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3c15416e3e6e40ddadb81498e71cdeef
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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