p-Toluenesulfonic acid → HCID 86599902, compound

HRID 902961Notes

Reaction equation

HRID 902961 reaction equation
[CH:1]12[CH2:8][NH:7][CH2:6][CH:5]1[CH2:4][N:3]([C:9]1[CH:21]=[CH:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12](=[O:22])[C:11]=3[CH:10]=1)[CH2:2]2.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>CO.CCOC(C)=O>[C:23]1([CH3:33])[CH:24]=[CH:25][C:26]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:27][CH:28]=1.[CH:5]12[CH2:6][NH:7][CH2:8][CH:1]1[CH2:2][N:3]([C:9]1[CH:21]=[CH:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12](=[O:22])[C:11]=3[CH:10]=1)[CH2:4]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11208526HCID 11208526, compound

Product 1

HCID 86599902HCID 86599902, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent2×

Procedure

To the product of Example 13B (50 mg, 0.17 mmol) in 10% CH3OH/EtOAc (2 mL) was added p-toluenesulfonic acid (33 mg, 0.17 mmol; Aldrich) in 10% CH3OH/EtOAc (1 mL). A precipitate formed which was isolated via filtration to give the title compound (68 mg, 0.13 mmol, 77% yield). 1H NMR (methanol-d4, 300 MHz): δ 7.70 (2H, m), 7.50 (1H, dt, J=7, 1 Hz), 7.43-7.48 (3H, m), 7.22 (2H, m), 7.17 (1H, dt, J=9, 4 Hz), 7.00 (1H, d, J=3 Hz), 6.83 (1H, dd, J=8, 2 Hz), 3.60 (2H, m), 3.52 (2H, m), 3.41 (2H, m), 3.20-3.27 (4H, m), 2.36 (3H, s). MS (DCl/NH3): m/z 291 (M+H)+. Anal. Calcd. for C19H8N2O.1.25C7H8O3S.0.8H2O: C, 64.09; H, 5.74; N, 5.39. Found: C, 63.71; H, 5.47; N, 5.80.

Workup

  1. customA precipitate formed which
  2. customwas isolated via filtration

Sources & evidence

ORD record
ord-ff23e08852cd4bfb9eec09622b5389ce
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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