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

HRID 1720802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720802
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3c15416e3e6e40ddadb81498e71cdeef
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506267

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