p-Toluenesulfonic acid monohydrate → HCID 18512737, compound

HRID 1370741Notes

Reaction equation

HRID 1370741 reaction equation
[C:1]([NH:4][CH:5]([CH2:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:6]([NH:8][O:9]C1CCCCO1)=[O:7])(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([NH:4][CH:5]([CH2:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:18])=[O:19])[C:6]([NH:8][OH:9])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18512741HCID 18512741, compound

Product 1

HCID 18512737HCID 18512737, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title compound of Example 15a (400 mg, 0.84 mmol) in methanol (40 mg), 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 flash chromatography (4:96 MeOH/CHCl3) yielded the title compound as a white solid (140 mg, 42%): Anal. Calcd. for C17H18N2O5S2.0.8H2O: C, 49.94; H, 4.83; N, 6.85; S, 15.68. Found: C, 50.23; H, 4.62; N, 6.80; S, 15.29.

Workup

  1. concentrationthe solution was concentrated
  2. customPurification by flash chromatography (4:96 MeOH/CHCl3)

Sources & evidence

ORD record
ord-30f0b0a983664b6aace7faf7c63588b4
Source dataset
uspto-grants-2003_06
Patent number
US06583299B1

Reaction notes

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