Water → (6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycine t-butyl ester

HRID 1720808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720808
[C:1]([O:18][CH:19]([CH2:27][O:28][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])[CH2:20][S:21][CH2:22][CH2:23][C:24]([OH:26])=O)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.[C:47]([O:51][C:52](=[O:59])[CH2:53][NH:54][C:55](=[O:58])[CH2:56][NH2:57])([CH3:50])([CH3:49])[CH3:48].P(C#N)(OCC)(OCC)=O.O>CN(C)C=O.C(N(CC)CC)C>[C:47]([O:51][C:52](=[O:59])[CH2:53][NH:54][C:55](=[O:58])[CH2:56][NH:57][C:24](=[O:26])[CH2:23][CH2:22][S:21][CH2:20][CH:19]([O:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:27][O:28][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])([CH3:50])([CH3:48])[CH3:49]

Komponenten

7

Edukt 4

HCID 962WaterHCID 76257Diethyl cyanophosphonateHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 86749434Glycylglycine t-butyl ester hydrochloride

Produkt 1

HCID 22418588(6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycine t-butyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 4 (200 mg) and glycylglycine t-butyl ester hydrochloride (80 mg) in dimethyl formamide (3 ml), triethylamine (0.099 ml) and diethyl cyanophosphate (73 mg) were added, followed by stirring at room temperature for 17 hours. After addition of water, the reaction mixture was extracted with chloroform. 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=1:3) to yield the title compound (191 mg, yield 78%) as a wax-like substance.

Aufarbeitung

  1. additionwere added
  2. extractionthe reaction mixture was extracted with chloroform
  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=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-3e526cf7a29b44729004db7b729a436c
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506267

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