Triethylamine → 2-Aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 3-(2-{9-[2-(1-tert-butoxycarbonyl-pyrrolidine-2-carbonyloxy)-acetyl]-5,7-dihydro-dibenzo[c,e]oxepin-3-yl}-2-oxo-ethyl) ester 2-tert-butyl ester

HRID 71708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 71708
[C:1]([O:5][C:6]([N:8]1[CH:13]([C:14]([OH:16])=[O:15])[CH:12]2[CH2:17][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:25]([O:29][C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH:33]1[C:37]([O:39][CH2:40][C:41]([C:43]1[CH:44]=[CH:45][C:46]2[C:52]3[CH:53]=[CH:54][C:55]([C:57](=[O:60])[CH2:58]Br)=[CH:56][C:51]=3[CH2:50][O:49][CH2:48][C:47]=2[CH:61]=1)=[O:42])=[O:38])=[O:31])([CH3:28])([CH3:27])[CH3:26]>C(#N)C.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:13]([C:14]([O:16][CH2:58][C:57]([C:55]2[CH:54]=[CH:53][C:52]3[C:46]4[CH:45]=[CH:44][C:43]([C:41](=[O:42])[CH2:40][O:39][C:37]([CH:33]5[CH2:34][CH2:35][CH2:36][N:32]5[C:30]([O:29][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:31])=[O:38])=[CH:61][C:47]=4[CH2:48][O:49][CH2:50][C:51]=3[CH:56]=2)=[O:60])=[O:15])[CH:12]2[CH2:17][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 150563882-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acidHCID 72337884Pyrrolidine-1,2-dicarboxylic acid 2-{2-[9-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-2-oxo-ethyl}ester 1-tert-butyl ester

Produkt 1

HCID 666199822-Aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 3-(2-{9-[2-(1-tert-butoxycarbonyl-pyrrolidine-2-carbonyloxy)-acetyl]-5,7-dihydro-dibenzo[c,e]oxepin-3-yl}-2-oxo-ethyl) ester 2-tert-butyl esterAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To the solution of 2-Aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester (100 mg, 0.42 mmol) and triethylamine (50 μl, 0.36 mmol) in acetonitrile (2 ml) was added a solution of pyrrolidine-1,2-dicarboxylic acid 2-{2-[9-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-2-oxo-ethyl}ester 1-tert-butyl ester (136 mg, 0.24 mmol) in DMF (4 ml). The mixture was stirred for 10 hours, and the solvent was evaporated. The mixture was diluted with EtOAc, and washed with water and brine, and was dried with sodium sulfate. Concentration gave 2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 3-(2-{9-[2-(1-tert-butoxycarbonyl-pyrrolidine-2-carbonyloxy)-acetyl]-5,7-dihydro-dibenzo[c,e]oxepin-3-yl}-2-oxo-ethyl) ester 2-tert-butyl ester (142 mg). m/z: 731.3 (M−H)−, 755.2 (M+Na)+.

Aufarbeitung

  1. customthe solvent was evaporated
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialwas dried with sodium sulfate
  5. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-e84d206cd041483996df515a5ffdf106
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

Notizen zur Reaktion

Wird geladen…