Trifluoroacetic acid → HCID 58118717, compound

HRID 1615823Notes

Reaction equation

HRID 1615823 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14](C(OC(C)(C)C)=O)[C:13](=[O:22])[C:12]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[NH:14][C:13](=[O:22])[C:12]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66864622HCID 66864622, compound

Product 1

HCID 58118717HCID 58118717, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (6S)-6-(3,5-difluorophenyl)-3,3-diethylpiperidin-2-one-1-carboxylate from Step D (1.22 g, 3.32 mmol) in CH2Cl2 (7 mL) at ambient temperature was added TFA (3 mL). After stirring for 1.5 h, the reaction mixture was concentrated in vacuo. The residue was partitioned between CH2Cl2 (30 mL) and saturated NaHCO3 (30 mL). The layers were separated and the aqueous layer was further extracted with CH2Cl2 (2×30 mL). The combined organics were dried over sodium sulfate, filtered and then concentrated in vacuo to provide the title compound, which could be used without further purification. MS: m/z=268 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between CH2Cl2 (30 mL) and saturated NaHCO3 (30 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was further extracted with CH2Cl2 (2×30 mL)
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cba2f22c88f0414d9c8c93d18b7150e2
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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