Acetonitrile → HCID 131723241, compound

HRID 1937828Notes

Reaction equation

HRID 1937828 reaction equation
C[O:2][C:3](=[O:36])[C@@H:4]([NH:11][C:12](=[O:35])[CH:13]([C:24](=[O:34])[N:25]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:26])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[NH:23])[NH2:22])=[CH:17][CH:16]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(#N)C.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].ClCCl>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[CH2:27]([N:25]([CH3:26])[C:24]([CH:13]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[NH:22])[NH2:23])=[CH:17][CH:16]=1)[C:12]([NH:11][C@@H:4]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C:3]([OH:36])=[O:2])=[O:35])=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 21863450Trifluoroacetic acid methylene chlorideHCID 131723242HCID 131723242, compound

Product 1

HCID 131723241HCID 131723241, compound

Procedure

22.1 g (44.8 mmol) of the above [2-(R,S)-(Benzyl-methyl-carbamoyl)-3-(4-carbamimidoyl-phenyl)-propionylamino]-(S)-cyclohexyl-acetic acid methyl ester was suspended in water/concentrated hydrochloric acid (1/1, 40 ml) and acetonitrile (40 ml) was added to give a solution. The reaction mixture was stirred at room temperature for 7 days. The reaction mixture was concentrated in vacuo and the residue was purified on silica gel with dichloromethane/methanol/TFA as solvent to give the desired product.

Workup

  1. customto give a solution
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified on silica gel with dichloromethane/methanol/TFA as solvent

Sources & evidence

ORD record
ord-6e8d72a1fdf04cc18bf1eb114d8e1aaf
Source dataset
uspto-grants-2002_05
Patent number
US06395737B1

Reaction notes

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