Trifluoroacetic acid → HCID 73603397, compound

HRID 627038Notes

Reaction equation

HRID 627038 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([C@@H:25]1[N:33]([C:34](=[O:53])[C@@H:35]([NH:39][C:40](=[O:52])[C@@H:41]([N:43](C)[C:44](=O)OC(C)(C)C)[CH3:42])[CH:36]([CH3:38])[CH3:37])[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH2:26]1)=[O:24])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([C@@H:25]1[N:33]([C:34](=[O:53])[C@@H:35]([NH:39][C:40](=[O:52])[C@@H:41]([NH:43][CH3:44])[CH3:42])[CH:36]([CH3:38])[CH3:37])[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH2:26]1)=[O:24])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735261HCID 131735261, compound

Product 1

HCID 73603397HCID 73603397, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL, 6.49 mmol, Eq: 127) was added to a solution of tert-butyl (R)-(2S)-1-((2S)-1-(2-(2-benzoylphenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (32 mg, 51.0 μmol, Eq: 1.00) in DCM (0.5 mL) and the resulting solution was stirred at rt for 2 h. The reaction mixture was concentrated in vacuo and the residue treated with saturated aqueous NaHCO3 (10 mL). The resulting mixture was extracted with EtOAc (1×10 mL) and the organic layer was concentrated in vacuo. The crude residue was treated with MeOH/DCM/ether to give (R)-1-[(S)-3-methyl-2-((S)-2-methylamino-propionylamino)-butyryl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-benzoyl-phenyl)-amide as an off-white solid (24 mg), m/z=528 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue treated with saturated aqueous NaHCO3 (10 mL)
  3. extractionThe resulting mixture was extracted with EtOAc (1×10 mL)
  4. concentrationthe organic layer was concentrated in vacuo
  5. additionThe crude residue was treated with MeOH/DCM/ether

Sources & evidence

ORD record
ord-6432db12582549278c714b59b72d91ad
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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