m-Chloroperbenzoic acid → HCID 86669681, compound

HRID 1623941Notes

Reaction equation

HRID 1623941 reaction equation
[S:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[C:11]3[CH2:12][C@H:13]4[CH2:26][C@H:14]4[C:15]=3[N:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[N:17]=2)=[O:9])[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:32]>C(Cl)Cl>[O:32]=[S:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[C:11]3[CH2:12][C@H:13]4[CH2:26][C@H:14]4[C:15]=3[N:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[N:17]=2)=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86669682HCID 86669682, compound

Product 1

HCID 86669681HCID 86669681, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (1aR,5aR)-2-(2,4-difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (tetrahydro-thiopyran-4-yl)-amide (0.014 g, 0.037 mmol) in anhydrous DCM (0.5 mL) was cooled to 0° C. on an ice bath. 3-Chlorobenzoperoxoic acid (7.08 mg, 0.041 mmol) in DCM (0.5 mL) was added drop wise and the reaction was stirred for 1 hour. The reaction mixture was extracted with DCM/water and NaHCO3. The organic phase was concentrated and the residue was purified by HPLC to provide the title compound (2.1 mg) as a white solid. LCMS m/z=392.5 [M+H]+.

Workup

  1. extractionThe reaction mixture was extracted with DCM/water and NaHCO3
  2. concentrationThe organic phase was concentrated
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-4a25f47f7ed14723b973472ff4afda60
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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