m-Chloroperbenzoic acid → HCID 17927086, compound

HRID 843145Notes

Reaction equation

HRID 843145 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:23][S:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1C=C(Cl)C=C(C(OO)=[O:41])C=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:23][S:24]([CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:41]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22615022HCID 22615022, compound

Product 1

HCID 17927086HCID 17927086, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a solution of the compound in Example 56 (20 mg, 0.04 mmol) in CH2Cl2/TFA (8/2) (1 ml) was added m-CPBA (14 mg, 80%, 0.06 mmol) at 0° C. The mixture was stirred for 2 hours at room temperature. The solvent was removed under reduced pressure. The residue was purified over preparative TLC (CH2Cl2/MeOH=100/1) to give the desired compound (7.5 mg, 36%) as a colorless oil. FAB-MS: m/z 463 (MH+); 1H-NMR (CDCl3): δ 1.97 (2H, m), 2.24 (3H, s), 2.81 (2H, t, J=6.9 Hz), 2.88-3.07 (4H, m), 3.77 (2H, s), 4.04-4.10 (4H, m), 6.52 (1H, d, J=7.6 Hz), 6.91 (1H, d, J=7.6 Hz), 7.05-7.22 (7H, m), 7.58 (1H, d, J=7.8 Hz) 8.41 (1H, brd, J=4.5 Hz), 8.48 (1H, brs).

Workup

  1. customat 0° C
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was purified over preparative TLC (CH2Cl2/MeOH=100/1)

Sources & evidence

ORD record
ord-6660128a6036492cad48ad061c8f53b0
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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