Trifluoroacetic acid → HCID 89813611, compound

HRID 525416Notes

Reaction equation

HRID 525416 reaction equation
[CH3:1][C:2]1([CH3:27])[O:6][C:5](=[O:7])[N:4]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[C@H:3]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:27])[O:6][C:5](=[O:7])[N:4]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[C@H:3]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89814338HCID 89814338, compound

Product 1

HCID 89813611HCID 89813611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 250-mL round-bottomed flask were added (S)-tert-butyl 4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)piperidine-1-carboxylate (4530 mg, 12.10 mmol) and 2,2,2-trifluoroacetic acid (23.16 mL, 302 mmol) in DCM (24.200 mL). The mixture was then stirred at rt overnight. The reaction mixture was concentrated in vacuo. The material thus obtained was dissolved in DCM, and extracted with water (3×). The aqueous layers were combined and the pH of the solution was adjusted to above 8 by adding 35% NH4OH water solution. The solution was then extracted with EtOAc (3×). The organic extract was dried over MgSO4. The solution was filtered and concentrated in vacuo to give the residual material as a yellow solid. The material was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe material thus obtained
  3. extractionextracted with water (3×)
  4. additionby adding 35% NH4OH water solution
  5. extractionThe solution was then extracted with EtOAc (3×)
  6. extractionThe organic extract
  7. dry with materialwas dried over MgSO4
  8. filtrationThe solution was filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5fc6b8f249d4f4f98227c37639fe953
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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