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

HRID 1040541Notes

Reaction equation

HRID 1040541 reaction equation
C([O:5][C:6](=[O:44])[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]([C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)=[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.O>[Cl:27][C:22]1[CH:21]=[C:20]([N:19]2[C:15]3=[N:14][CH:13]=[C:12]([C:10]([NH:9][C@@H:7]([CH3:8])[C:6]([OH:44])=[O:5])=[O:11])[N:16]3[C@@:17]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=4)=[CH:33][CH:32]=3)([CH3:29])[C:18]2=[O:28])[CH:25]=[C:24]([Cl:26])[CH:23]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58430916(S)-2-{[(R)-7-(3,5-dichloro-phenyl)-5-(4'-fluoro-biphenyl-4-ylmethyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid tert-butyl ester

Product 1

HCID 58431048(S)-2-{[(R)-7-(3,5-dichloro-phenyl)-5-(4'-fluoro-biphenyl-4-ylmethyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-{[(R)-7-(3,5-dichloro-phenyl)-5-(4′-fluoro-biphenyl-4-ylmethyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid tert-butyl ester (0.15 g, 0.24 mmol) in CH2Cl2 (10 mL) was added TFA (4 mL) and the mixture stirred at room temperature for 12 h. The mixture was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water, brine and dried with MgSO4. The mixture was filtered and concentrated to give 120 mg of (S)-2-{[(R)-7-(3,5-dichloro-phenyl)-5-(4′-fluoro-biphenyl-4-ylmethyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid as a white solid, m/z 581.3 [M]+.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried with MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a06ba7e329404f13b84758f244c75eb8
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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