m-Chloroperbenzoic acid → HCID 11705114, compound

HRID 2217776Notes

Reaction equation

HRID 2217776 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-3ba1c32891bd4480a512dfcfabbeca79
Source dataset
uspto-grants-2008_08
Patent number
US07408068B2

Reaction notes

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