Trifluoroacetic acid → (R)-1-(4-Guanidino-phenyl)-pyrrolidine-2-carboxylic acid methylamide

HRID 1441377Notes

Reaction equation

HRID 1441377 reaction equation
C(OC([NH:8]/[C:9](/[NH:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:33][CH2:32][CH2:31][C@@H:26]2[C:27]([NH:29][CH3:30])=[O:28])=[CH:21][CH:20]=1)=[N:10]/C(OC(C)(C)C)=O)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[K+]>C(Cl)Cl>[CH3:30][NH:29][C:27]([C@H:26]1[CH2:31][CH2:32][CH2:33][N:25]1[C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:9]([NH2:10])=[NH:8])=[CH:20][CH:21]=1)=[O:28]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 178485742HCID 178485742, compound

Product 1

HCID 178485743(R)-1-(4-Guanidino-phenyl)-pyrrolidine-2-carboxylic acid methylamideYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-[4-({(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)phenyl]-N-methyl-D-prolinamide (Method 58; 1.9 g) was added DCM (60 ml) and TFA (20 ml). The reaction was stirred for 4 hours before removal of the solvent in vacuo. The reaction was basified with 2.0N KOH (20 ml) and extracted with DCM (2×50 ml). Product failed to extract in to DCM, the aqueous was reduced down to 90% of the initial volume and re-extracted with DCM (3×200 ml), dried and solvent removed in vacuo to yield the title compound as a brown solid (0.84 g, 78%). NMR (299.955 MHz) 7.79 (q, 1H), 7.57 (s, 1H), 7.18 (s, 2H), 7.03 (d, 2H), 6.48 (d, 2H), 3.91 (d, 1H), 3.58-3.54 (m, 1H), 3.17 (q, 1H), 2.56 (d, 3H), 2.19-2.09 (m, 2H), 2.01-1.89 (m, 2H); m/z 261.

Workup

  1. extractionextracted with DCM (2×50 ml)
  2. extractionto extract in to DCM
  3. extractionre-extracted with DCM (3×200 ml)
  4. customdried
  5. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-8c7dd7c906fa436d9156b1b8f1188554
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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