m-Chloroperbenzoic acid → HCID 15035377, compound

HRID 483413Notes

Reaction equation

HRID 483413 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:13][CH:14]=3)[C:9]([S:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:8]2[CH2:27][C:28]([OH:30])=[O:29])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([CH3:19])([CH3:17])[CH3:18])=[CH:13][CH:14]=3)[C:9]([S:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:41])=[C:8]2[CH2:27][C:28]([OH:30])=[O:29])=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15035376HCID 15035376, compound

Product 1

HCID 15035377HCID 15035377, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a cold (-10°) solution of 1-(p-chlorobenzyl)-5-(t-butyl)-3-phenylthioindole-2-acetic acid (67 mg) from Example 12 in 1.45 mL dry methylene chloride, under nitrogen, was added 34 mg of m-chloroperbenzoic acid. The reaction mixture was stirred at -10° for 1 h and room temperature for 30 min. The reaction mixture was then diluted with ether and washed with water (2×) and brine and dried over MgSO4. Filtration and concentration gave a solid which was passed through a short column of silica gel. Elution with ethyl acetate gave the title compound, mp 160°-161° (dec.).

Workup

  1. washwashed with water (2×) and brine
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and concentration
  4. customgave a solid which
  5. washElution with ethyl acetate

Sources & evidence

ORD record
ord-40a20d6ea0df46e8901e1e9720069a5b
Source dataset
uspto-grants-1993_07
Patent number
US05225421

Reaction notes

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