m-Chloroperbenzoic acid → (S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxide

HRID 931825Notes

Reaction equation

HRID 931825 reaction equation
[Br:1][C:2]1[C:11]([C@H:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:24])=[N:7]2.ClC1C=C(C=CC=1)C(OO)=[O:30]>ClCCl>[Br:1][C:2]1[C:11]([C@H:12]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:24])=[N+:7]2[O-:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68586165(S)-ethyl 2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetate

Product 1

HCID 66631477(S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-ethyl 2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetate (5H) (500 mg, 1.27 mmol) in dichloromethane (13 mL) at 0° C. was added 3-chloroperoxybenzoic acid (269 mg, 77%, 1.21 mmol) and the reaction mixture was allowed to slowly warm to room temperature over 3 hours. The reaction mixture was partitioned between ethyl acetate and water and the organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes and methanol/ethyl acetate) to give a yellow oil (497 mg, 95%). LCMS-ESI+ (m/z): [M]+ calcd for C19H2413rNO4: 410.3;

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. concentrationthe organic layer was concentrated
  3. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes and methanol/ethyl acetate)

Sources & evidence

ORD record
ord-c8ceaf53221740d2ac97586b6191d299
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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