m-Chloroperbenzoic acid → HCID 58615466, compound

HRID 2222956Notes

Reaction equation

HRID 2222956 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:39])[C@@H:12]([N:24]2[C:28](=[O:29])[CH:27]([C:30]3[CH:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][CH:31]=3)[NH:26][C:25]2=[O:38])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[S:8][CH:9]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:48])C=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:39])[C@@H:12]([N:24]2[C:28](=[O:29])[CH:27]([C:30]3[CH:31]=[CH:32][C:33]([S:36]([CH3:37])=[O:48])=[CH:34][CH:35]=3)[NH:26][C:25]2=[O:38])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[S:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11505173HCID 11505173, compound

Product 1

HCID 58615466HCID 58615466, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(S)-2-[4-(4-methylsulfanyl-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-(2-trifluoromethyl-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester (95 mg, 0.16 mmol) in dichloromethane (15 mL) was added 3-chloroperbenzoic acid (75% purity) (45 mg, 0.19 mmol) at 0° C. After stirring for 10 minute the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was dried over sodium sulfate, filtered, concentrated and the residue was purified by chromatography over silica gel eluted with acetone. The isolated material was precipitated from acetone with an excess of hexanes to afford 2-[(S)-2-[4-(4-methanesulfinyl-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-(2-trifluoromethyl-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester as an amorphous white solid (50 mg, 52%).

Workup

  1. customwas partitioned between ethyl acetate and saturated aqueous sodium carbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by chromatography over silica gel
  6. washeluted with acetone
  7. customThe isolated material was precipitated from acetone with an excess of hexanes

Sources & evidence

ORD record
ord-6a1b1e3ae4514e4eba14bf02fbff5722
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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