HCID 14181640, Verbindung → HCID 14798654, Verbindung

HRID 232196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 232196
O=[C:2]([CH2:16][CH2:17][C:18]([O-:20])=[O:19])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:4].[CH2:21]([O:28][C:29]([NH:31][C@H:32]1[CH2:36][O:35][NH:34][C:33]1=[O:37])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl.B(F)(F)F.CCOCC>[CH2:21]([O:28][C:29]([NH:31][C@H:32]1[CH2:36][O:35][N:34]([C:2]2([C:3]([O:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=3)=[O:4])[CH2:16][CH2:17][C:18](=[O:19])[O:20]2)[C:33]1=[O:37])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 2

HCID 14181640HCID 14181640, VerbindungHCID 221664155-[(4-Nitrophenyl)methoxy]-4,5-dioxopentanoate

Produkt 1

HCID 14798654HCID 14798654, VerbindungAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8000Boron trifluoride etherateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 5 ml of dichloromethane were dissolved 155 mg of Compound (1) and 119 mg of (4S)-4-benzyloxycarbonylamino-3-isoxazolidinone. To the solution were added two drops of boron trifluoride etherate (47% ether solution) and 2 g of Molecular Sieves (3A). The mixture was allowed to stand at room temperature for 2 days. The reaction solution, after removing the Molecular Sieves, was washed with a cooled aqueous solution of sodium hydrogen carbonate, followed by drying (MgSO4). The solvent was evaporated off under reduced pressure, and the residue was purified by subjecting to a silica gel preparative thin-layer chromatography [developed with 1,2-dichloroethane-ethyl acetate (5:1)] to give 12.5 mg of the subject Compound (9).

Aufarbeitung

  1. customThe reaction solution, after removing the Molecular Sieves
  2. washwas washed with a cooled aqueous solution of sodium hydrogen carbonate
  3. dry with materialby drying (MgSO4)
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-c4b49d8d204444ebbc239fb8bcb5e13d
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851422

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