Trifluoroacetic acid → HCID 71542004, compound

HRID 1850209Notes

Reaction equation

HRID 1850209 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:16]([C@H:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:33]=[N:34][N:35]([CH3:37])[CH:36]=3)=[CH:28][CH:27]=2)[CH3:25])C(=O)OC(C)(C)C)[N:11]=1)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:33]=[N:34][N:35]([CH3:37])[CH:36]=3)=[CH:28][CH:27]=2)[CH3:25])[N:11]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86730164HCID 86730164, compound

Product 1

HCID 71542004HCID 71542004, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl((S)-1-(4-(1-methyl-1H-pyrazol-4-yl)phenyl)ethyl)carbamate (45 mg, 0.09 mmol) in DCM (1 mL) was added TFA (1 mL, 12 mmol) slowly at −78° C. The reaction was stirred at room temperature for 1 h then was concentrated and diluted with DCM (10 mL). The solution was washed with saturated NaHCO3 solution and brine. After separation, the aqueous phase was extracted with DCM (3×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated to give (S)-4-isopropyl-3-(2-(((S)-1-(4-(1-methyl-1H-pyrazol-4-yl)phenyl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one as a white solid (35 mg, 97% yield).

Workup

  1. concentrationthen was concentrated
  2. additiondiluted with DCM (10 mL)
  3. washThe solution was washed with saturated NaHCO3 solution and brine
  4. customAfter separation
  5. extractionthe aqueous phase was extracted with DCM (3×10 mL)
  6. dry with materialCombined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-925ae5b9c9df426ca43c29dc8d3ba6e4
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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