Tetrabutylammonium Fluoride → allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 382638

Reaktionsgleichung

Reaktionsgleichung von HRID 382638
[Si]([O:8][C@@H:9]([C@H:11]1[C:32](=[O:33])[N:13]2[C:14]([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])=[C:15]([C:18]3[N:19]=[CH:20][N:21]4[CH:25]=[CH:24][S:23][C:22]=34)[C@H:16]([CH3:17])[C@H:12]12)[CH3:10])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[OH:8][C@@H:9]([C@H:11]1[C:32](=[O:33])[N:13]2[C:14]([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])=[C:15]([C:18]3[N:19]=[CH:20][N:21]4[CH:25]=[CH:24][S:23][C:22]=34)[C@H:16]([CH3:17])[C@H:12]12)[CH3:10]

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 131722910allyl (1S,5R,6S)-6-((1R)-1-t-butyldimethylsilyloxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

Produkt 1

HCID 131722909allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylateAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 460 mg of allyl (1S,5R,6S)-6-((1R)-1-t-butyldimethylsilyloxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 14 ml of THF were added 860 μl and 3.76 ml of a 1 M tetra-n-butylammonium fluoride in THF, and the mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with 120 ml of ethy acetate, washed with 30 ml of semi-saturated aqueous saline, and then with 30 ml of a mixed solution of semi-saturated aqueous saline and a saturated aqueous sodium hydrogen carbonate solution (1:1), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (dichloromethane:methanol=97:3-95:5) to give 286 mg of allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Aufarbeitung

  1. washwashed with 30 ml of semi-saturated aqueous saline
  2. dry with materialwith 30 ml of a mixed solution of semi-saturated aqueous saline and a saturated aqueous sodium hydrogen carbonate solution (1:1), dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by column chromatography on silica gel (dichloromethane:methanol=97:3-95:5)

Quellen und Nachweise

ORD-Eintrag
ord-1ae473a85fcd4f6d99e224557a6b3cfd
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310056B1

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