Trifluoroacetic acid → HCID 117887617, compound

HRID 1477170Notes

Reaction equation

HRID 1477170 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[NH:16][C:17]([C@@H:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]1[C:28](=[O:47])[C@@H:29]([NH:33][C:34](=[O:46])[C@@H:35]([N:37](C)[C:38](=O)OC(C)(C)C)[CH3:36])[CH:30]([CH3:32])[CH3:31])=[O:18]>C(Cl)Cl>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[NH:16][C:17]([C@@H:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]1[C:28](=[O:47])[C@@H:29]([NH:33][C:34](=[O:46])[C@@H:35]([NH:37][CH3:38])[CH3:36])[CH:30]([CH3:31])[CH3:32])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736481HCID 131736481, compound

Product 1

HCID 117887617HCID 117887617, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL, 26.0 mmol, Eq: 96.7) was added to a solution of tert-butyl (S)-1-((S)-1-((S)-2-(2,6-difluorophenylcarbamoyl)indolin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (0.15 g, 269 μmol, Eq: 1.00) in DCM (2 mL) and the resulting solution was stirred at rt for 1 hr. The reaction mixture was concentrated in vacuo and treated with minimal ether/hexanes to give (S)-1-[(S)-3-methyl-2-((S)-2-methylamino-propionylamino)-butyryl]-2,3-dihydro-1H-indole-2-carboxylic acid (2,6-difluoro-phenyl)-amide as a white solid (0.11 g), m/z=459 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiontreated with minimal ether/hexanes

Sources & evidence

ORD record
ord-36b23e0f74d4476ba4cf450b51a155ef
Source dataset
uspto-grants-2016_08
Patent number
US09403768B2

Reaction notes

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