Phosphate → benzhydryl (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1247774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247774
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:38]/[O:39][C:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])([CH3:42])[CH3:41])/[C:8]([NH:10][C@@H:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18]Cl)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[I-:50].[Na+].P([O-])([O-])([O-])=O.C(OCC)(=O)C>C1(C)C=CC=CC=1.[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.O>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:38]/[O:39][C:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])([CH3:42])[CH3:41])/[C:8]([NH:10][C@@H:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18][I:50])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Komponenten

8

Edukt 4

HCID 1061PhosphateHCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 87787298benzhydryl (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Produkt 1

HCID 87844717benzhydryl (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 77620884Tricaprylylmethyl ammonium chlorideLösungsmittel

Versuchsvorschrift

To a solution of benzhydryl 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (60 g) in toluene (600 ml) were added a solution of sodiumiodide (61.8 g) in 0.05 mol phosphate buffer (pH 7, 500 ml) and tricaprylylmethylammonium chloride (6.67 g). The mixture was stirred at room temperature for 15 hours. The reaction mixture was added to a mixture of ethyl acetate and water. The organic layer was washed with water and brine, and then dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated to 255 g under reduced pressure. The concentrate was poured into diisopropyl ether (2 L). The resulting precipitate was collected by filtration and dried to give benzhydryl 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-iodomethyl-3-cephem-4-carboxylate (59.4 g).

Aufarbeitung

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. customthe filtrate was evaporated to 255 g under reduced pressure
  5. additionThe concentrate was poured into diisopropyl ether (2 L)
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d24e9c35c4594a029def2e0e2f2ebd9e
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129232B2

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