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

HRID 327616Notes

Reaction equation

HRID 327616 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-76b67b25b518494d9dc51c93ecb84d52
Source dataset
uspto-grants-1993_12
Patent number
US05273990

Reaction notes

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