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

HRID 1040537Notes

Reaction equation

HRID 1040537 reaction equation
C([O:5][C:6](=[O:38])[C@@H:7]([NH:9][C:10]([C:12]1[N:16]2[C@@:17]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=3)([CH3:29])[C:18](=[O:28])[N:19]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)[C:15]2=[N:14][CH:13]=1)=[O:11])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][C@@:17]2([CH3:29])[N:16]3[C:12]([C:10]([NH:9][C@@H:7]([CH3:8])[C:6]([OH:38])=[O:5])=[O:11])=[CH:13][N:14]=[C:15]3[N:19]([C:20]3[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=3)[C:18]2=[O:28])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58430923(S)-2-{[(R)-5-(4-bromo-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid tert-butyl ester

Product 1

HCID 58431145(S)-2-{[(R)-5-(4-bromo-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acidYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-{[(R)-5-(4-bromo-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid tert-butyl ester (3.0 g, 4.8 mmol) in CH2Cl2 (20 mL) was added TFA (1 mL). The reaction was allowed to stir for 30 minutes and then the solvent removed in vacuo to afford 2.2 g of (S)-2-{[(R)-5-(4-bromo-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid as a white solid, m/z 442.2 [M+]+.

Workup

  1. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3f6a0a9fcf6145ed820d496153d1a328
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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