Triethylamine → HCID 67953258, compound

HRID 469738Notes

Reaction equation

HRID 469738 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][C@H:16]([OH:18])[CH2:15][N:14]2[C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][N:20]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CS(C)=O>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][C:16](=[O:18])[CH2:15][N:14]2[C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:27])([F:28])[F:29])=[CH:21][N:20]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 8471Triethylamine2×HCID 67458577HCID 67458577, compound

Product 1

HCID 67953258HCID 67953258, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (2S,4S)-1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-4-hydroxy-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (183 mg, 0.423 mmol) in dimethyl sulfoxide (5 mL) is added triethylamine (0.118 mL, 0.846 mmol) and sulfur trioxide pyridine complex (115 mg, 0.72 mmol). The reaction is stirred at room temperature for 4 hours. More triethylamine (0.18 mL, 1.27 mmol) and sulfur trioxide pyridine complex (155 mg, 0.97 mmol) are added to the reaction mixture and the stirring is continued for another 2 hours. The reaction is quenched with 1N hydrochloric acid aqueous solution and the solid precipitated out of the solution is filtered and dissolved in dichloromethane and washed with saturated sodium bicarbonate aqueous solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by chromatography on silica eluting with ethyl acetate/hexanes and further purification using pre LC-MS provides the title compound, ESI m/z 431 [M+H+].

Workup

  1. waitthe stirring is continued for another 2 hours
  2. customThe reaction is quenched with 1N hydrochloric acid aqueous solution
  3. customthe solid precipitated out of the solution
  4. filtrationis filtered
  5. dissolutiondissolved in dichloromethane
  6. washwashed with saturated sodium bicarbonate aqueous solution and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by chromatography on silica eluting
  11. customwith ethyl acetate/hexanes and further purification

Sources & evidence

ORD record
ord-ed139746b0db4f59aa5b503091de8ef0
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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