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Isobutyl iodide → 1,3-Dihydro-5-(1,1-dimethylethyl)1-(2-Methylpropyl)-3(R,S)-[(benzyloxycarbonyl)-amino]-2H-1,4benzodiazepin-2-one

HRID 2399686
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2399686
[CH3:1][C:2]([C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[CH:7]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[N:6]=1)([CH3:4])[CH3:3].[H-].[Na+].[CH3:30][CH:31]([CH3:34])[CH2:32]I>CN(C)C=O>[CH3:4][C:2]([C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:30][CH:31]([CH3:34])[CH3:32])[C:8](=[O:16])[CH:7]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[N:6]=1)([CH3:1])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 135722083HCID 135722083, Verbindung

Produkt 1

HCID 101369981,3-Dihydro-5-(1,1-dimethylethyl)1-(2-Methylpropyl)-3(R,S)-[(benzyloxycarbonyl)-amino]-2H-1,4benzodiazepin-2-oneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A solution of 1,3-dihydro-5-(1,1-dimethylethyl)-3(R,S) -[(benzyloxycarbonyl)-amino]-2H-1,4-benzodiazepin-2-one (500 mg, 1.4 mmol) in dimethylformamide (10 ml) under an atmosphere of nitrogen, was treated with sodium hydride (54 mg of a 57% dispersion in mineral oil, 1.4 mol) in one portion at 0° C. After 1 h, 2-methylpropyl iodide (0.17 ml, 1.45 mmol) was added and the resulting mixture stirred at room temperature for 16 h. The solvent was then evaporated and the crude residue partitioned between water (15 ml) and dichloromethane (2×20 ml). The combined organic phases were washed with brine (2×20 ml), dried (MgSO4) and evaporated. The residue was chromatographed on silica using 2:1 petrol:ethyl acetate as eluent, to afford the title compound as a colourless solid (320 mg, 56%). 1H NMR (250 MHz, D6 -DMSO) δ 0.63 (3H, d, J=7 Hz), 0.77 (3H, d, J=7 Hz), 1.26 (9H, s), 1.49 (1H, m), 3.56 (1H, dd, J=4 Hz, 14 Hz), 4.10 (1H, dd, J=4 Hz, 14 Hz), 4.88 (1H, m), 5.02 (2H, m), 7.20-7.40 (5H, m), 7.58 (1H, t, J=8 Hz), 7.66 (1H, d, J=9 Hz), 7.77 (1H, d, J=8 Hz), 8.18 (1H, d, J=9 Hz).

Aufarbeitung

  1. customThe solvent was then evaporated
  2. customthe crude residue partitioned between water (15 ml) and dichloromethane (2×20 ml)
  3. washThe combined organic phases were washed with brine (2×20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica using 2:1 petrol

Quellen und Nachweise

ORD-Eintrag
ord-a07045179234472ea70bb1f9bbe439ac
Quelldatensatz
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05451582

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