m-Chloroperbenzoic acid → HCID 118254188, compound

HRID 1483148Notes

Reaction equation

HRID 1483148 reaction equation
[CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[Cl:12][C:13]1[C:33]2[O:32][C@:19]3([C@H:28]([CH3:29])[CH2:27][C:26]4[N:25]=[C:24]([CH3:30])[CH:23]=[CH:22][C:21]=4[C:20]3=[O:31])[C:18](=[O:34])[C:17]=2[C:16]([O:35][CH3:36])=[CH:15][C:14]=1[O:37][CH3:38]>ClCCl>[Cl:12][C:13]1[C:33]2[O:32][C@:19]3([C@H:28]([CH3:29])[CH2:27][C:26]4[N:25]=[C:24]([CH2:30][CH3:1])[CH:23]=[CH:22][C:21]=4[C:20]3=[O:31])[C:18](=[O:34])[C:17]=2[C:16]([O:35][CH3:36])=[CH:15][C:14]=1[O:37][CH3:38]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 90034429HCID 90034429, compound

Product 1

HCID 118254188HCID 118254188, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottomed flask 1.3 g (7.7 mmol, 2 eq.) of mCPBA was added to a solution of (2S,7′R)-7-chloro-4,6-dimethoxy-2′,7′-dimethyl-7′,8′-dihydro-3H,5′H-spiro[benzofuran-2,6′-quinoline]-3,5′-dione (1.5 g, 3.9 mmol, 1.0 eq) in 45 mL of dichloromethane. The mixture was left under agitation at ambient temperature for 16 h, then concentrated under reduced pressure. The residue was dissolved in AcOEt. The organic phase was washed with 10% Na2S2O3 solution, then a saturated NaHCO3 solution, then brine solution and dried over Na2SO4, filtered and concentrated under reduced pressure. A yellow solid (1.6 g) was obtained with a yield of 100%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in AcOEt
  3. washThe organic phase was washed with 10% Na2S2O3 solution
  4. dry with materiala saturated NaHCO3 solution, then brine solution and dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12fa68b2707940bda85d46d382b4c348
Source dataset
uspto-grants-2016_08
Patent number
US09416143B2

Reaction notes

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