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Ammonium nitrate → 2-(3-Amino-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

HRID 1599089
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1599089
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([N:13]([CH:22]([CH3:24])[CH3:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:12])[C:6]2[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=2[N:4](CC2C=CC(OC)=CC=2)[C:3]1=[O:38].[N+]([O-])([O-])=O.[NH4+]>C(#N)C.O>[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([N:13]([CH:22]([CH3:24])[CH3:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:12])[C:6]2[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=2[NH:4][C:3]1=[O:38]
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Komponenten

4

Edukt 2

HCID 22985Ammonium nitrateHCID 189295902-[3-Amino-5-(4-methoxybenzyl)-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)-acetamide

Produkt 1

HCID 189295732-(3-Amino-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamideAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)
Lösungsmittel

Versuchsvorschrift

To a stirred solution of 2-[3-Amino-5-(4-methoxybenzyl)-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)-acetamide (2.63 g, 5.09 mmol) in acetonitrile/H2O (9:1, 70 mL) at ambient temperature was added cerric ammonium nitrate (10.05 g, 18.3 mmol) portionwise over one hour. The solution was stirred overnight at room temperature. The solution was concentrated in vacuo, chased with toluene (2×50 mL) and the residue was extracted with CH2Cl2 (3×50 mL), filtered and concentated to an orange glass. The crude product was purified by flash chromatography on silica gel (100 g) eluting successively with CH2 Cl2 /CH3OH (15:1, 1.5 L) and CH2Cl2 /CH3OH (10:1, 1.3 L). Appropriate fractions were combined and concentrated under reduced pressure to give the title compound (1.97 g, 4.97 mmol) as a brown foam: 1H NMR (300 MHz, DMSO-d6): d 10.68 (br s, 1H), 7.39-6.98 (m, 8H), 5.75 (s, 1H), 4.76 (m, 1H), 4.16-3.92 (m, 4H), 3.7 (s, 3H), 3.15 (m, 2H), 0.97 (m, 6H); TLC (CH2Cl2 /CH3OH (13:1)): Rf =0.21.

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. extractionthe residue was extracted with CH2Cl2 (3×50 mL)
  3. filtrationfiltered
  4. customThe crude product was purified by flash chromatography on silica gel (100 g)
  5. washeluting successively with CH2 Cl2 /CH3OH (15:1, 1.5 L) and CH2Cl2 /CH3OH (10:1, 1.3 L)
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d071d168adaf4af0b784dd036badba19
Quelldatensatz
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05739129

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