Trifluoroacetic acid → HCID 67034433, compound

HRID 539044Notes

Reaction equation

HRID 539044 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]2[N:16]=[CH:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[N:29]=[CH:28][N:27]([CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[N:26]=4)=[CH:21][CH:20]=3)=[C:12]2[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]2[N:16]=[CH:17][C:18]([C:19]3[CH:20]=[CH:21][C:22]([C:25]4[N:29]=[CH:28][N:27]([CH2:30][C:31]([OH:33])=[O:32])[N:26]=4)=[CH:23][CH:24]=3)=[C:12]2[N:11]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67035301HCID 67035301, compound

Product 1

HCID 67034433HCID 67034433, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-tert-butyl 2-(3-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1H-1,2,4-triazol-1-yl)acetate (66 mg, 0.13 mmol) in DCM (1 mL) was added dropwise TFA (1 mL) at 0° C. under N2. The reaction mixture was stirred at ambient temperature overnight. The solvents were evaporated in vacuo. The residue was dissolved in saturated aqueous NaHCO3 solution and washed with Ether. The aqueous layer was acidified by slow addition of 1N HCl. The mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated to give (S)-2-(3-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1H-1,2,4-triazol-1-yl)acetic acid (48 mg, 82%). LCMS (APCI+) m/z 448.3 [M+H]+.

Workup

  1. customThe solvents were evaporated in vacuo
  2. dissolutionThe residue was dissolved in saturated aqueous NaHCO3 solution
  3. washwashed with Ether
  4. additionThe aqueous layer was acidified by slow addition of 1N HCl
  5. extractionThe mixture was extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ff74cb8d92c64d12b511ca5f4d6c5b24
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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