m-Chloroperbenzoic acid → HCID 178501781, compound

HRID 1593230Notes

Reaction equation

HRID 1593230 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[N:7]=[C:8]([S:10][CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[C:15]([CH3:21])=[CH:14][N:13]=3)[NH:9][C:5]=2[C:4]=1[S:24]([C:27]1[C:38]([CH3:39])=[CH:37][C:30]([O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:29][C:28]=1[CH3:40])(=[O:26])=[O:25].ClC1C=C(C=CC=1)C(OO)=[O:46]>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[N:7]=[C:8]([S:10]([CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[C:15]([CH3:21])=[CH:14][N:13]=3)=[O:46])[NH:9][C:5]=2[C:4]=1[S:24]([C:27]1[C:28]([CH3:40])=[CH:29][C:30]([O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:37][C:38]=1[CH3:39])(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178501779HCID 178501779, compound2×

Product 1

HCID 178501781HCID 178501781, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solutions of methyl {4-[(5-methoxy-2{[4-methoxy,3,5-dimethyl(2-pyridyl)methyl]thio}benzimidazolyl)sulfonyl]-3,5-dimethylphenoxy}acetate (Intermediate A5, 7.1 g, 0.12 mol) in 100 mL of tetrahydrofuran and 3-chloroperoxybenzoic acid (2.6 g, 0.15 mol) in 20 mL of the same solvent were cooled in a freezer for 1 hr and then mixed. The solution was left in the freezer for about 16 hr, diluted with ethyl acetate, and washed with several portions each of 5% sodium metabisulfite, 5% sodium bicarbonate, and saturated sodium chloride. The organic phase was concentrated and then purified on flash silica gel (hexanes→ethyl acetate→1% methanol in ethyl acetate). The title compound recovered weighed 3.3 g (46%).

Workup

  1. additionmixed
  2. washwashed with several portions each of 5% sodium metabisulfite, 5% sodium bicarbonate, and saturated sodium chloride
  3. concentrationThe organic phase was concentrated
  4. custompurified on flash silica gel (hexanes→ethyl acetate→1% methanol in ethyl acetate)
  5. customThe title compound recovered

Sources & evidence

ORD record
ord-9c11719a08904cc69cc4611b6d97cdb2
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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