Ammonium Chloride → (2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester

HRID 411777

Reaktionsgleichung

Reaktionsgleichung von HRID 411777
[Li]CC[CH2:4][CH3:5].[OH:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=3)[N:16]([CH3:26])[CH:15]=2)=[C:10]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH3:36])[CH:28]=2)[C:9]1=[O:37].[N+](C1C=CC(OC(=O)OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=[O:39].[NH2:60][CH:61]([OH:63])C.[NH4+].[Cl-]>C1COCC1>[CH3:36][N:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]([C:10]2[C:9](=[O:37])[N:8]([CH2:7][O:6][C:61](=[O:63])[NH:60][CH2:4][CH2:5][OH:39])[C:12](=[O:13])[C:11]=2[C:14]2[C:22]3[C:17](=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=3)[N:16]([CH3:26])[CH:15]=2)=[CH:28]1

Komponenten

7

Edukt 5

HCID 25517Ammonium ChlorideHCID 78756Bis(4-nitrophenyl) carbonateHCID 522583Acetaldehyde ammoniaHCID 98673381-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dioneHCID 178418339Butyllithium

Produkt 1

HCID 9892774(2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl esterAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

n-BuLi (0.96 mL, 1.54 mmol, 1.6 M in hexanes) was added drop-wise to a solution of 1-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (600 mg, 1.54 mmol), prepared as in example la, in THF (30 mL) at 0° C. After 10 min bis(p-nitrophenyl)carbonate (600 mg, 1.96 mmol) was added. The solution was stirred at 0° C. for 20 min. A solution of 1-aminoethanol (128 mg, 2.10 mmol) was added. The resulting mixture was stirred at 0° C. for 30 min. Aqueous NH4Cl was added and the mixture was extracted with EtOAc. The organic extract was washed with brine and dried over MgSO4. Evaporation of the solvents and chromatography of the residue over silica gel using 1:1-3:2 EtOAc/hexanes gave (2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester (339 mg, 47%).

Aufarbeitung

  1. customat 0° C
  2. stirringThe resulting mixture was stirred at 0° C. for 30 min
  3. extractionthe mixture was extracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvents and chromatography of the residue over silica gel using 1:1-3:2 EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ad09b47b9b6040e4ac0dc4c003cf5548
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559164B1

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