Trifluoroacetic acid → HCID 86664822, compound

HRID 1628242Notes

Reaction equation

HRID 1628242 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:31])[C@@H:15]([NH:23]C(=O)OC(C)(C)C)[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:10]([CH3:32])[N:9]=2)[CH:5]=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:23][C@@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([NH:13][C:11]1[N:10]([CH3:32])[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[CH:12]=1)=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86664823HCID 86664823, compound

Product 1

HCID 86664822HCID 86664822, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 250 ml flask was added 18.8 g of tert-butyl (S)-1-(3-(2-chloropyridin-4-yl)-1-methyl-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 1.D, 100 ml of DCM and 50 ml of TFA. The reaction was stirred at room temperature for 4 hours at which time the solvent was removed with a stream of nitrogen. The crude was partitioned between 2000 ml of DCM and 500 ml of saturated aqueous sodium bicarbonate. The organic layer was extracted twice more with 500 ml of water, dried over sodium sulfate and the organic solvent was removed by rotary evaporation. The crude was purified using a silica gel column (eluting with 5% MeOH in DCM) to give 8.6 g of (2S)-2-amino-N-(3-(2-chloropyridin-4-yl)-1-methyl-1H-pyrazol-5-yl)-3-phenylpropanamide 17.7.E as a light brown solid.

Workup

  1. customwas removed with a stream of nitrogen
  2. customThe crude was partitioned between 2000 ml of DCM and 500 ml of saturated aqueous sodium bicarbonate
  3. extractionThe organic layer was extracted twice more with 500 ml of water
  4. dry with materialdried over sodium sulfate
  5. customthe organic solvent was removed by rotary evaporation
  6. customThe crude was purified
  7. washa silica gel column (eluting with 5% MeOH in DCM)

Sources & evidence

ORD record
ord-e988161521014d379fc78d7d2042c4d9
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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