Sodium Hydroxide → HCID 58123859, compound

HRID 536653Notes

Reaction equation

HRID 536653 reaction equation
[F-].[K+].[C:3]([C:5]1[C:6](OS(C(F)(F)F)(=O)=O)=[CH:7][C:8]2[C@@:15]3([CH3:18])[C@H:16]([CH3:17])[C@H:11]([N:12](C(=O)C(F)(F)F)[CH2:13][CH2:14]3)[CH2:10][C:9]=2[CH:25]=1)#[N:4].[OH-].[Na+]>O.O1CCCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:18][C@:15]12[C@H:16]([CH3:17])[C@H:11]([NH:12][CH2:13][CH2:14]1)[CH2:10][C:9]1[CH:25]=[C:5]([C:3]#[N:4])[CH:6]=[CH:7][C:8]2=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 522689Potassium FluorideHCID 58497736HCID 58497736, compound

Product 1

HCID 58123859HCID 58123859, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of KF (76 mg) in water (1 mL) followed by polymethylhydrosiloxane (1.0 g) is added to a mixture of (2R,6R,11S)-trifluoro-methanesulfonic acid 9-cyano-6,11-dimethyl-3-(2,2,2-trifluoro-acetyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl ester (0.30 g) and Pd(OAc)2 (7 mg) in tetrahydrofuran (3 mL). The resulting mixture is stirred at room temperature overnight before 1 M NaOH (20 mL) is added. After stirring vigorously for 1 h, the organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water and brine and dried (MgSO4). The solvent is removed and the residue is taken up in 4 M NaOH (1 mL) and methanol (3 mL) and stirred at room temperature overnight. Then, the solution is neutralized with 1 M hydrochloric acid, filtered, concentrated and the residue is purified by HPLC on reversed phase (MeCN/water).

Workup

  1. additionis added
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washThe combined organic phases are washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed
  7. stirringmethanol (3 mL) and stirred at room temperature overnight
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue is purified by HPLC on reversed phase (MeCN/water)

Sources & evidence

ORD record
ord-f416907bd7dd46e6949d9f66684674fb
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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