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Pyridine → 3-(4(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one

HRID 1582358
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Reaktionsgleichung

Reaktionsgleichung von HRID 1582358
Cl.[NH:2]1[CH2:7][CH2:6][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:17][C:16]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1.N1C=CC=CC=1.[CH3:33][C:34]1([CH3:42])[O:38][C@H:37]([C:39](Cl)=[O:40])[CH2:36][O:35]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:33][C:34]1([CH3:42])[O:38][C@H:37]([C:39]([N:2]2[CH2:7][CH2:6][C:5]([C:8]3[C:13]([F:14])=[CH:12][C:11]([N:15]4[CH2:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:17][C:16]4=[O:25])=[CH:10][C:9]=3[F:26])=[CH:4][CH2:3]2)=[O:40])[CH2:36][O:35]1
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Komponenten

6

Edukt 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 10374773HCID 10374773, VerbindungHCID 20725654HCID 20725654, Verbindung

Produkt 1

HCID 207256423-(4(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-oneAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-(4-(1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one hydrochloride (14.5 g, 37.3 mM) was suspended in dry dichloromethane (300 ml) under nitrogen at 0°, and treated with pyridine (9.78 g, 0.12 M). A solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (9.59 g, 75.6 mM) in dichloromethane (100 ml) was added dropwise, and stirring continued for 3 hours, allowing the temperature to rise to ambient. Aqueous sodium bicarbonate (5%, 300 ml) was added, and stirring continued for 30 minutes. The organic phase was separated, dried (magnesium sulfate), filtered, and evaporated to dryness after the addition of toluene (20 ml). The solid residue was triturated with a mixture of diethyl ether (250 ml) and isohexane (150 ml), and solid filtered to give the title compound (17.5 g). NMR (DMSO-d6) δ: 1.30 (2×s, 6H); 2.02 (s, 3H); 2.28 (br, 1H); 2.39 (br, 1H); 3.67 (t overlapping m, 2H); 3.83 (dd, 1H); 4.00-4.32 (overlapping m, 7H); 4.90 (overlapping m, 2H); 5.86 (s, 1H); 7.34 (d, 2H). MS (ESP): 481 (MH+) for C23H26F2N2O7

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 30 minutes
  3. customThe organic phase was separated
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. additionafter the addition of toluene (20 ml)
  8. customThe solid residue was triturated with a mixture of diethyl ether (250 ml) and isohexane (150 ml), and solid
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-5ad9f41e6e474c98afcbdca0163d0f05
Quelldatensatz
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06734200B1

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