Acetonitrile → (2S)-1-{(2S)-2-[(1S)-1-(ethoxycarbonyl)butylamino]propionyl}-2,3,4,5,6,7-hexa-hydro-1H-indole-2-carboxylic acid

HRID 2221318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221318
[NH2:1][C@@H:2]([CH2:8][CH2:9][CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.C(#N)C.Br[C@H:22]([CH3:37])[C:23]([N:25]1[C:33]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=2[CH2:27][C@H:26]1[C:34]([OH:36])=[O:35])=[O:24]>ClCCl>[CH2:6]([O:5][C:3]([C@@H:2]([NH:1][C@@H:22]([CH3:37])[C:23]([N:25]1[C:33]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=2[CH2:27][C@H:26]1[C:34]([OH:36])=[O:35])=[O:24])[CH2:8][CH2:9][CH3:10])=[O:4])[CH3:7]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 10080526ethyl (2S)-2-aminopentanoateHCID 69308328(2S)-1-[(2R)-2-bromopropionyl]-2,3,4,5,6,7-hexahydro-1H-indole-2-carboxylic acid

Produkt 1

HCID 11152800(2S)-1-{(2S)-2-[(1S)-1-(ethoxycarbonyl)butylamino]propionyl}-2,3,4,5,6,7-hexa-hydro-1H-indole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Introduce into a reactor 105 g of ethyl (2S)-2-aminopentanoate, 135 ml of triethylamine and 135 ml of acetonitrile, and then bring the mixture to 60° C. and slowly add a solution of 200 g of the compound obtained in Step A in 1.3 litres of dichloromethane, and subsequently reflux for 4 hours. After returning to ambient temperature, wash the mixture with water and with a dilute acetic acid solution, and then evaporate off the solvents to yield (2S)-1-{(2S)-2-[(1S)-1-(ethoxycarbonyl)butylamino]propionyl}-2,3,4,5,6,7-hexa-hydro-1H-indole-2-carboxylic acid.

Aufarbeitung

  1. customto 60° C.
  2. temperaturesubsequently reflux for 4 hours
  3. customAfter returning to ambient temperature
  4. washwash the mixture with water
  5. customwith a dilute acetic acid solution, and then evaporate off the solvents

Quellen und Nachweise

ORD-Eintrag
ord-434a4a94378041729b8f4ceefc0a28ce
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368580B2

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