p-Toluenesulfonic acid → HCID 58932572, compound

HRID 853857Notes

Reaction equation

HRID 853857 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22])(=[O:11])=[O:10].[CH2:23](O)[CH2:24][CH2:25][OH:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]12[O:26][CH2:25][CH2:24][CH2:23][O:22]1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 9883721HCID 9883721, compound

Product 1

HCID 58932572HCID 58932572, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a rapidly and efficiently stirred mixture of 5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione (4.21 g, 13.0 mmol) in benzene (300 mL), was added 1,3-propanediol (3.81 mL, 52 mmol, 4 eq) and p-toluenesulfonic acid (0.989 g, 5.2 mmol, 0.4 mole % ) and the reaction was refluxed with a Dean Stark Trap for 4.5 hours under a dry N2 atmosphere. After cooling to room temperature the reaction was washed with sat. aq. NaHCO3 (3×), water (3×), brine (3×), dried over MgSO4, and concentrated. The crude product was purified on Biotage KP silica gel eluting with 50/50 Pet ether/EtOAc to give the title compound as a white solid (1.34 g, 27% yield). NMR (400 MHz, DMSO-d6): consistent; MS: (API-ES−) m/z 381 [M−H]. MS: (API+ES+) m/z 383 [M+H].

Workup

  1. temperaturethe reaction was refluxed with a Dean Stark Trap for 4.5 hours under a dry N2 atmosphere
  2. washwas washed with sat. aq. NaHCO3 (3×), water (3×), brine (3×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified on Biotage KP silica gel eluting with 50/50 Pet ether/EtOAc

Sources & evidence

ORD record
ord-a0e9e79665754c38b2e87589d153b9a9
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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