Sodium Iodide → HCID 10175121, Verbindung

HRID 1070895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070895
[C:1]([C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:24])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@@H:17]1[C:21]([OH:23])=[O:22])=[O:15])([OH:3])=[O:2].Cl[CH2:26][C:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28].[I-].[Na+].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37].CN(C)C=[O:46]>>[CH2:30]([N:29]([CH2:32][CH3:33])[C:27]([CH2:26][O:22][C:21]([C@H:17]1[CH2:18][CH2:19][CH2:20][N:16]1[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@@H:4]1[C:1]([O:3][CH2:37][C:36](=[O:46])[N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])=[O:2])=[O:24])=[O:23])=[O:28])[CH3:31]

Komponenten

6

Edukt 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 16844Chloro-N,N-diethylacetamideHCID 125516Miridesap

Produkt 1

HCID 10175121HCID 10175121, VerbindungAusbeute 92 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 170 mg (0.5 mmol) (R)-1-[6-[(R)-2-carboxy-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid and 137 ml (1 mmol) 2-chloro-N,N-diethylacetamide in 3 ml dimethylformamide were added 14.9 mg (0.1 mmol) sodium iodide and 139 ml (1 mmol) triethylamine. After stirring overnight at 90° C. the solvent was distilled off, the residue was taken up with dichloromethane and extracted with water. The organic extracts were dried with sodium sulfate and the solvent was distilled off to yield 260 mg (92%) of (R)-1-{6-[(R)-2-(diethylcarbamoyl-methoxycarbonyl)-pyrrolidin-1-yl]-6-oxo-hexanoyl}-pyrrolidine-2-carboxylic acid diethylcarbamoyl-methyl ester as a yellow oil, MS m/e (%): 567 (M+H+, 100).

Aufarbeitung

  1. distillationwas distilled off
  2. extractionextracted with water
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-3cd242875e324798acfaa863b852dedf
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903129B2

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