p-Toluenesulfonic acid monohydrate → HCID 86601089, compound

HRID 902979Notes

Reaction equation

HRID 902979 reaction equation
[C@@H:1]12[CH2:7][NH:6][C@@H:5]1[CH2:4][N:3]([C:8]1[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:21])[C:10]=3[CH:9]=1)[CH2:2]2.O.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>CCOC(C)=O.CCO>[C:23]1([CH3:33])[CH:24]=[CH:25][C:26]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:27][CH:28]=1.[C@@H:1]12[CH2:7][NH:6][C@@H:5]1[CH2:4][N:3]([C:8]1[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:21])[C:10]=3[CH:9]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67163860HCID 67163860, compound

Product 1

HCID 86601089HCID 86601089, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of the product of Example 39B (60 mg, 0.22 mmol) and p-toluenesulfonic acid monohydrate (48 mg, 0.25 mmol) was stirred in EtOAc-EtOH (4 mL, 10:1) at room temperature for 16 h. The resulted solid was collected and dried under vacuum to afford the title compound (63 mg, 0.13 mmol; 58% yield): 1H NMR (300 MHz, CD3OD) δ ppm 7.70 (2H, d, J=8 Hz), 7.44-7.57 (4H, m), 7.17-7.26 (4H, m), 7.05 (1H, dd, J=8, 3 Hz), 5.03 (1H, dd, J=7, 5 Hz), 4.26 (1H, dd, J=11, 9 Hz), 4.16 (1H, d, J=13 Hz), 3.94 (1H, d, J=11 Hz), 3.76 (1H, dd, J=11, 5 Hz), 3.44-3.55 (1H, m), 3.15 (1H, dd, J=13, 5 Hz), 3.06 (1H, dd, J=11, 6 Hz), 2.36 (3H, s): MS (DCl/NH3): m/z 277 (M+1)+. Anal. Calcd. for C18H16N2O.1.3C7H8O3S: C, 65.07; H, 5.32; N, 5.60. Found: C, 64.88; H, 5.20; N, 5.68.

Workup

  1. customThe resulted solid was collected
  2. customdried under vacuum

Sources & evidence

ORD record
ord-fdf7375c253b47e38702abf7f4a15ac2
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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