Trifluoroacetic acid → HCID 73295229, compound

HRID 1485906Notes

Reaction equation

HRID 1485906 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:41])[C@@H:23]([NH:27][C:28](=[O:40])[C@@H:29]([N:31](C)[C:32](=O)OC(C)(C)C)[CH3:30])[CH:24]([CH3:26])[CH3:25])=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[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:41])[C@@H:23]([NH:27][C:28](=[O:40])[C@@H:29]([NH:31][CH3:32])[CH3:30])[CH:24]([CH3:26])[CH3:25])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736769HCID 131736769, compound

Product 1

HCID 73295229HCID 73295229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-1-((S)-1-((S)-3-(2,6-difluorophenylcarbamoyl)-3,4-dihydro isoquinolin-2 (1H)-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (138 mg, 241 μmol, Eq: 1.00) in DCM (2 mL) was added TFA (2.96 g, 2 mL, 26.0 mmol, Eq: 108) and the resulting solution stirred at RT for 1 h. The mixture was concentrated in vacuo, saturated NaHCO3 was added to the residue and the resulting mixture extracted with DCM. The combined extracts were dried over Na2SO4 and concentrated in vacuo. The residue was treated with ether/hexanes to give (S)-2-[(S)-3-methyl-2-((S)-2-methylamino-propionylamino)-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (2,6-difluoro-phenyl)-amide as a white solid which was used without purification (70 mg), m/z=473 (M+H).

Workup

  1. concentrationThe mixture was concentrated in vacuo, saturated NaHCO3
  2. additionwas added to the residue
  3. extractionthe resulting mixture extracted with DCM
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. additionThe residue was treated with ether/hexanes

Sources & evidence

ORD record
ord-8f88afc6416c44158d09989e60f8733c
Source dataset
uspto-grants-2016_08
Patent number
US09422332B2

Reaction notes

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