(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate → HCID 66631760, compound

HRID 931821Notes

Reaction equation

HRID 931821 reaction equation
[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH:41]([Mg]Br)([CH3:43])[CH3:42].O1CCCC1>O1CCCC1.CN1CCCC1=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe]>[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH:41]([CH3:43])[CH3:42])[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

5

Reactant 2

HCID 86691982(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate2×HCID 178420663HCID 178420663, compound

Product 1

HCID 66631760HCID 66631760, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 11110968Iron (III) acetylacetonateCatalystHCID 22156051tetrahydrofuran N-methylpyrrolidinoneSolvent

Procedure

To a solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26) (200 mg, 0.33 mmol) and iron (III) acetylacetonate (6 mg, 0.017 mmol) in anhydrous tetrahydrofuran/1-methyl-2-pyrrolidinone (5 mL/0.5 mL) at 0° C. was added 2.9 M in tetrahydrofuran isopropylmagnesium bromide (0.149 mL, 0.431 mmol) drop wise. The reaction was let warm to room temperature over three hours, quenched with water and extracted with ethyl acetate and concentrated. The crude reaction was purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a yellow oil (77 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C30H39ClNO3: 496.25. found: 496.83.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated
  4. customThe crude reaction
  5. customwas purified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-312972618bff4e7198b876c74dafa37e
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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