N-tert-Butoxycarbonyl-L-tryptophan → (3S)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one

HRID 963465

Reaktionsgleichung

Reaktionsgleichung von HRID 963465
C(OC(N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1)=O)(C)(C)C.[NH2:23][CH:24]1[N:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[C:28]2[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=2[N:26]([CH2:42][C:43]([N:45]2[CH2:51][CH:50]3[CH2:52][CH2:53][CH:47]([CH2:48][CH2:49]3)[CH2:46]2)=[O:44])[C:25]1=[O:54]>C(#N)C.C(Cl)Cl>[NH2:23][C@H:24]1[N:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[C:28]2[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=2[N:26]([CH2:42][C:43]([N:45]2[CH2:51][CH:50]3[CH2:52][CH2:53][CH:47]([CH2:48][CH2:49]3)[CH2:46]2)=[O:44])[C:25]1=[O:54]

Komponenten

5

Edukt 2

HCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 19081160(3RS)-1-{(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl}-3-amino-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Produkt 1

HCID 54425021(3S)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-oneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-tert-butoxycarbonyl-L-tryptophan (0.70 g) in acetonitrile (20 ml) was added dropwise a solution of (3RS)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (1.00 g) in methylene chloride (5 ml) under stirring at ambient temperature. The mixture was stirred overnight. The precipitate was collected by filtration and the colorless solid was partitioned between methylene chloride and 0.5N NaOH. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford (3S)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (0.46 g) as s colorless crystal.

Aufarbeitung

  1. stirringThe mixture was stirred overnight
  2. filtrationThe precipitate was collected by filtration
  3. customthe colorless solid was partitioned between methylene chloride and 0.5N NaOH
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b138eac3035940ed844fdebad43ac9a4
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763437

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