2-Methylbenzenesulfonic acid → HCID 12018150, compound

HRID 1017586Notes

Reaction equation

HRID 1017586 reaction equation
C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[C:23](=[O:43])[NH:24][C:25](=[O:42])[C:26]=2[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33][CH2:34][C@H:35]3[CH2:39][O:38]C(C)(C)[O:36]3)[CH:28]=2)=[CH:14]1>CO.O>[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[C:23](=[O:43])[NH:24][C:25](=[O:42])[C:26]=2[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33][CH2:34][C@H:35]([OH:36])[CH2:39][OH:38])[CH:28]=2)=[CH:14]1

Participants

5

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 12018149HCID 12018149, compound

Product 1

HCID 12018150HCID 12018150, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Toluenesulfonic acid (10 mg) was added to a solution of 3-(1-methylindol-3-yl)-4-{3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethylsulfanyl)phenyl]-1H-pyrrole-2,5-dione (60 mg) in methanol (10 mL) and water (1 mL) and the reaction mixture was heated at 50° C. for 2 h. The volatiles were removed and the residue was partitioned between water and EtOAc. The organic layer was washed with NaCl (sat.) and dried over sodium sulfate. The crude product was purified on a silica gel column with 10/45/45 of MeOH/CH2Cl2/hexane and further purified by recrystallization from CH2Cl/hexane to give 3-(1-methylindol-3-yl)-4-[3-((R)-2,3-dihydroxypropylsulfanyl)phenyl]-1H-pyrrole-2,5-dione (47 mg). MS (EI): M+ 408.

Workup

  1. customThe volatiles were removed
  2. customthe residue was partitioned between water and EtOAc
  3. washThe organic layer was washed with NaCl (sat.)
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified on a silica gel column with 10/45/45 of MeOH/CH2Cl2/hexane
  6. customfurther purified by recrystallization from CH2Cl/hexane

Sources & evidence

ORD record
ord-cf41ce346765480cacd5f1c7af11207a
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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