p-Toluenesulfonic acid monohydrate → HCID 12074755, compound

HRID 1370739Notes

Reaction equation

HRID 1370739 reaction equation
[O:1]=[C:2]([NH:28][O:29]C1CCCCO1)[CH:3]([NH:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:29][NH:28][C:2]([CH:3]([NH:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:13]=1)(=[O:6])=[O:7])=[O:1]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18512747HCID 18512747, compound

Product 1

HCID 12074755HCID 12074755, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title compound of Example 11f (500 mg, 0.96 mmol) in methanol (20 mL) was added p-toluenesulfonic acid, monohydrate (40 mg, 0.21 mmol). After stirring at room temperature for 2 hours, the solution was concentrated. Purification by chromatography (6:94 MeOH/CHCl3) yielded the title compound as a light beige solid (170 mg, 40%): Anal. Calcd. for C20H24N2O5S2.0.5 H2O: C, 53.91; H, 5.66; N, 6.29; S, 14.39. Found: C, 53.98; H, 5.44; N, 6.20; S, 14.47.

Workup

  1. concentrationthe solution was concentrated
  2. customPurification by chromatography (6:94 MeOH/CHCl3)

Sources & evidence

ORD record
ord-2e17d6bc551f4efcbbeeecadac12234b
Source dataset
uspto-grants-2003_06
Patent number
US06583299B1

Reaction notes

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