m-Chloroperbenzoic acid → HCID 70975843, compound

HRID 535522Notes

Reaction equation

HRID 535522 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][N:12]2[N:21]=[C:20]([S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:29])=[O:10])=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:35]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][N:12]2[N:21]=[C:20]([S:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:35])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:29])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70976126HCID 70976126, compound

Product 1

HCID 70975843HCID 70975843, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Example 58 (0.0200 g, 0.047 mmol) and 3-chlorobenzoperoxoic acid (0.0125 g, 0.051 mmol) in DCM (0.5 mL) was stirred at room temperature for 1 hour, diluted with EtOAc, washed with sat NaHCO3 and brine, dried (Na2SO4), filtered, and chromatographed (8-10% EtOAc/DCM) to give 4.5 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.90 (s, 1H), 8.44-8.48 (m, 1H), 8.30-8.34 (m, 1H), 7.86-7.96 (m, 2H), 7.70-7.76 (m, 2H), 7.50-7.61 (m, 3H), 7.38-7.46 (m, 4H), 3.76 (s, 2H); MS (ESI−) M/Z 436 (M−H)−.

Workup

  1. washwashed
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customchromatographed (8-10% EtOAc/DCM)

Sources & evidence

ORD record
ord-8e02c0725a9941b3b771fea64f118b0e
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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