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Benzylamine → 11-(4S)-{2-[(benzylaminomethyl)-dimethylsilanyl]-ethyl}-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

HRID 2246530
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2246530
Cl[CH2:2][Si:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C>[CH2:34]([NH:41][CH2:2][Si:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
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Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 2522749711-(4S)-[2-(chloromethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Produkt 1

HCID 5765938011-(4S)-{2-[(benzylaminomethyl)-dimethylsilanyl]-ethyl}-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dioneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

A solution of Compound 3 (100 mg) and benzylamine (70 μL) in acetonitrile (2 mL) was heated at 110° C. over 8 hours. Solvent was removed under reduced pressure and the crude product was stirred in trifluoroacetic acid (1 mL) for 2 hours at room temperature. Finally, trifluoroacetic acid was removed under reduced pressure and the crude product was partitioned between chloroform (20 mL) and 7% aqueous NaHCO3 solution (10 mL). The chloroform layer was dried and concentrated and purified on a silica gel column using 4% ethanol in dichloromethane to obtain the product in 50% yield (57 mg).

Aufarbeitung

  1. customSolvent was removed under reduced pressure
  2. customFinally, trifluoroacetic acid was removed under reduced pressure
  3. customthe crude product was partitioned between chloroform (20 mL) and 7% aqueous NaHCO3 solution (10 mL)
  4. dry with materialThe chloroform layer was dried
  5. concentrationconcentrated
  6. custompurified on a silica gel column
  7. customto obtain the product in 50% yield (57 mg)

Quellen und Nachweise

ORD-Eintrag
ord-e0bb8012f9ed4b06b6a4a64a618783a4
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07687496B2

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