Tetrahydrofuran → HCID 67815309, compound

HRID 2401393Notes

Reaction equation

HRID 2401393 reaction equation
[NH2:1][C@@H:2]([C:7]1[O:11][N:10]=[C:9]([CH3:12])[C:8]=1[C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15](OCC)=[O:16])[C:3]([F:6])([F:5])[F:4].C1COCC1.C([Mg]Cl)(C)C>[NH4+].[Cl-].CCOC(C)=O>[CH3:12][C:9]1[C:8]2[C:13]3[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=3[C:15](=[O:16])[NH:1][CH:2]([C:3]([F:6])([F:5])[F:4])[C:7]=2[O:11][N:10]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 67814345HCID 67814345, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67815309HCID 67815309, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-40 °C

Procedure

To a round bottomed flask was added ethyl 2-(5-((S)-1-amino-2,2,2-trifluoroethyl)-3-methylisoxazol-4-yl)benzoate (124.2 mg, 0.378 mmol) and THF (2 mL) before the solution was cooled to −40° C. To this solution was added isopropylmagnesium chloride (473 μl, 0.946 mmol) and the reaction warmed to room temperature. The solution was diluted with NH4Cl solution and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford the titled compound (86 mg, 0.305 mmol). LC/MS m/z 283 [M+H]+.

Workup

  1. temperaturethe reaction warmed to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-9783ba924db749dcaed382746bc386d5
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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