Trifluoroacetic acid → (S)-3-[5-(1-amino-2-biphenyl-4-yl-ethyl)-tetrazol-1-yl]-propionitrile trifiuoroacetate salt

HRID 327616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327616
C(OC([NH:8][C@H:9]([C:23]1[N:27]([CH2:28][CH2:29][C:30]#[N:31])[N:26]=[N:25][N:24]=1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>C(Cl)Cl>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[NH2:8][C@H:9]([C:23]1[N:27]([CH2:28][CH2:29][C:30]#[N:31])[N:26]=[N:25][N:24]=1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 54083632(S)-3-[5-(1-t-butoxycarbonylamino-2-biphenyl-4-yl-ethyl)tetrazol-1-yl]-propionitrile

Produkt 1

HCID 22849543(S)-3-[5-(1-amino-2-biphenyl-4-yl-ethyl)-tetrazol-1-yl]-propionitrile trifiuoroacetate salt

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-3-[5-(1-t-butoxycarbonylamino-2-biphenyl-4-yl-ethyl)-tetrazol-1-yl]-propionitrile (9.22 g, 22 mmol) is dissolved in methylene chloride (135 mL) under nitrogen. To the stirred solution is added trifluoroacetic acid (50 mL). After 50 minutes, the solution is concentrated under reduced pressure and the residue is treated with ether (200 mL). The amorphous solid is filtered off, washed with ether and dried under vacuum at 45° for 2 hours, then at room temperature for 18 hours to yield (S)-3-[5-(1-amino-2-biphenyl-4-yl-ethyl)-tetrazol-1-yl]-propionitrile trifluoroacetate salt, m.p. 211°-212°, [α]D =+23.35° (c 1.05, DMSO).

Aufarbeitung

  1. concentrationthe solution is concentrated under reduced pressure
  2. additionthe residue is treated with ether (200 mL)
  3. filtrationThe amorphous solid is filtered off
  4. washwashed with ether
  5. customdried under vacuum at 45° for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-76b67b25b518494d9dc51c93ecb84d52
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273990

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