Trifluoroacetic acid → HCID 118252532, compound

HRID 1485905Notes

Reaction equation

HRID 1485905 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]([C@@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1[C:22](=[O:35])[C@@H:23]([NH:27]C(=O)OC(C)(C)C)[CH:24]([CH3:26])[CH3:25])=[O:11].[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C(Cl)Cl>[F:39][C:38]([F:41])([F:40])[C:36]([OH:42])=[O:37].[NH2:27][C@@H:23]([CH:24]([CH3:26])[CH3:25])[C:22]([N:13]1[C@H:12]([C:10]([NH:9][C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[O:11])[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736768HCID 131736768, compound

Product 1

HCID 118252532HCID 118252532, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-1-((S)-3-(2,6-difluorophenylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-methyl-1-oxobutan-2-ylcarbamate (0.11 g, 226 μmol, Eq: 1.00) in DCM (2 mL) was added TFA (2.96 g, 2 mL, 26.0 mmol, Eq: 115) and the resulting solution was stirred at RT for 1 h. The reaction mixture was concentrated in vacuo and the residue azeotroped with n-heptanes to give (S)-2-((S)-2-amino-3-methylbutanoyl)-N-(2,6-difluorophenyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide trifluoroacetate which was used without purification (0.11 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue azeotroped with n-heptanes

Sources & evidence

ORD record
ord-0734fbb5fbc545e78ccb222856f2ba4d
Source dataset
uspto-grants-2016_08
Patent number
US09422332B2

Reaction notes

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