Trifluoroacetic acid → 1-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid

HRID 1040522Notes

Reaction equation

HRID 1040522 reaction equation
C([O:5][C:6]([C:8]1([NH:11][C:12]([C:14]2[N:18]3[C@@:19]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=4)([CH3:31])[C:20](=[O:30])[N:21]([C:22]4[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=4)[C:17]3=[N:16][CH:15]=2)=[O:13])[CH2:10][CH2:9]1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:39]([C:36]1[CH:37]=[CH:38][C:33]([CH2:32][C@@:19]2([CH3:31])[N:18]3[C:14]([C:12]([NH:11][C:8]4([C:6]([OH:7])=[O:5])[CH2:9][CH2:10]4)=[O:13])=[CH:15][N:16]=[C:17]3[N:21]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=3)[C:20]2=[O:30])=[CH:34][CH:35]=1)#[N:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 584312301-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid tert-butyl ester

Product 1

HCID 584309681-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid tert-butyl ester (3.8 g, 6.55 mmol) was dissolved in CH2Cl2 (100 mL), and. TFA (20 mL) was then added dropwise to the solution. The mixture was stirred overnight. After evaporation of the solvent in vacuo, the residue was purified by flash chromatography on silica gel (5% MeOH/CH2Cl2) to give 1-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-α]imidazole-3-carbonyl]-amino}-cyclopropane-carboxylic acid (3.4 g, 6.48 mmol, 99.0%) as a white solid, m/z 524.3 [M+1]+.

Workup

  1. customAfter evaporation of the solvent in vacuo
  2. customthe residue was purified by flash chromatography on silica gel (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ceb4d97e58244a289881fa107dea6cf9
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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