m-Chloroperbenzoic acid → HCID 11705114, compound

HRID 852344Notes

Reaction equation

HRID 852344 reaction equation
[CH3:1][C:2]([C:7]1[S:11][C:10]([NH:12][C:13](=[O:30])[CH:14]([NH:18][C:19](=[O:29])[CH2:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=2)[CH2:15][CH2:16][CH3:17])=[N:9][N:8]=1)([CH3:6])[CH2:3][CH:4]=[CH2:5].ClC1C=CC=C(C(OO)=[O:39])C=1>C(Cl)Cl>[CH3:1][C:2]([C:7]1[S:11][C:10]([NH:12][C:13](=[O:30])[CH:14]([NH:18][C:19](=[O:29])[CH2:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=2)[CH2:15][CH2:16][CH3:17])=[N:9][N:8]=1)([CH3:6])[CH2:3][CH:4]1[CH2:5][O:39]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11539372HCID 11539372, compound

Product 1

HCID 11705114HCID 11705114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoic acid [5-(1,1-dimethyl-but-3-enyl)-[1,3,4]thiadiazol-2-yl]-amide (196 mg, 0.45 mmol) and ˜60% pure m-chloroperbenzoic acid (109 mg, 0.45 mmol) in methylene chloride was stirred for 4 hr. The mixture was quenched with water, saturated Na2S2O3 and extracted with methylene chloride. The organic layer was washed with brine, separated, dried, and concentrated to give 114 mg of crude material with a mixture of desired title compound and undesired N-oxide and recovered starting material. The crude material was purified by HPLC and the title compound was isolated, LC-MS, RT=2.3 min, M=1=453.5.

Workup

  1. customThe mixture was quenched with water, saturated Na2S2O3
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. customseparated
  5. customdried
  6. concentrationconcentrated
  7. customto give 114 mg of crude material

Sources & evidence

ORD record
ord-7162297d8ab84878956b3ae768c4f030
Source dataset
uspto-grants-2007_08
Patent number
US07253195B2

Reaction notes

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