Propanedioyl dichloride → tert-butyl (2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetate

HRID 1375354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375354
[NH:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](Cl)(=[O:28])[CH2:24][C:25](Cl)=[O:26]>C1COCC1>[O:26]=[C:25]1[N:14]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:23](=[O:28])[CH2:24]1

Komponenten

4

Edukt 2

HCID 74269Propanedioyl dichlorideHCID 69425039tert-butyl N-(2-anilinophenyl)glycinate

Produkt 1

HCID 86602389tert-butyl (2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To 100 mL of THF at 0° C. was added dropwise over 20 min simultaneously a solution of the tert-butyl N-(2-anilinophenyl)glycinate (9.5 g, 31.8 mM) in 100 mL of THF and solution of malonyl dichloride (5.38 mL, 38.21 mM) in 100 mL of THF. The resulting solution was stirred at RT for 20 h and the solvent removed in vacuo. The resultant material was purified by silica gel flash column chromatography using hexanes/EtOAc 6/14 and the combined filtrates evaporated in vacuo to give 10.2 g of product. 1H NMR (DMSO-d6) 1.40 (s, 9H), 3.19 (d, J=12 Hz, 1H), 3.69 (d, J=12 Hz, 1H), 4.55 (d, J=17 Hz, 1H), 4.71 (d, J=17 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 7.20 (t, J=8 Hz, 1H), 7.33 (m, 4H), 7.46 (m, 3H).

Aufarbeitung

  1. customthe solvent removed in vacuo
  2. customThe resultant material was purified by silica gel flash column chromatography
  3. customthe combined filtrates evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-678afc13401744dc8b7cabd8de2e9a1e
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169773B2

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