m-Chloroperbenzoic acid → HCID 58427948, compound

HRID 1473789Notes

Reaction equation

HRID 1473789 reaction equation
[CH3:1][O:2][N:3]1[CH2:33][CH2:32][C:6]2([N:10]([O:11][CH2:12][CH2:13][S:14][CH3:15])[C:9](=[O:16])[C:8]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])=[C:7]2[O:26][C:27](=[O:31])[O:28][CH2:29][CH3:30])[CH2:5][CH2:4]1.ClC1C=CC=C(C(OO)=[O:42])C=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>ClCCl>[CH3:15][S:14]([CH2:13][CH2:12][O:11][N:10]1[C:6]2([CH2:5][CH2:4][N:3]([O:2][CH3:1])[CH2:33][CH2:32]2)[C:7]([O:26][C:27](=[O:31])[O:28][CH2:29][CH3:30])=[C:8]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[C:9]1=[O:16])=[O:42]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 58428051HCID 58428051, compound

Product 1

HCID 58427948HCID 58427948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of carbonic acid ethyl ester 8-methoxy-1-(2-methylsulfanyl-ethoxy)-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester (compound P1ii.110) (400 mg, 0.84 mmol) in dichloromethane (10 ml) at 0° C. was added 3-chloroperbenzoic acid (210 mg, MCPBA ˜70%, 0.85 mmol). The reaction mixture was stirred at room temperature overnight, then poured on saturated aqueous sodium metabisulfite and the layers separated. The aqueous phase was extracted with dichloromethane (3×), the combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol 20:1). Yield: 220 mg of carbonic acid ethyl ester 1-(2-methanesulfinyl-ethoxy)-8-methoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester (title compound P1ii.111) as a colorless gum.

Workup

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted with dichloromethane (3×)
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol 20:1)

Sources & evidence

ORD record
ord-c707f82da9904236a8557d5988eee904
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

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