p-Toluenesulfonic acid monohydrate → HCID 86599903, compound

HRID 553035Notes

Reaction equation

HRID 553035 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]3[C:17]4[CH:18]=[CH:19][C:20]([O:22][C@H:23]5[CH:28]6[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]6)[CH2:24]5)=[CH:21][C:16]=4[S:15][C:14]=3[CH:31]=1)[CH2:2]2.O.[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39]([OH:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1>C(OCC)(=O)C.C(O)C>[C:33]1([CH3:43])[CH:34]=[CH:35][C:36]([S:39]([OH:42])(=[O:40])=[O:41])=[CH:37][CH:38]=1.[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@H:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]3[C:17]4[CH:18]=[CH:19][C:20]([O:22][C@H:23]5[CH:28]6[CH2:27][CH2:26][N:25]([CH2:30][CH2:29]6)[CH2:24]5)=[CH:21][C:16]=4[S:15][C:14]=3[CH:31]=1)[CH2:2]2

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11293451HCID 11293451, compound

Product 1

HCID 86599903HCID 86599903, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 18A (150 mg, 0.32 mmol) was dissolved in ethyl acetate (5 mL) and ethanol (0.2 mL), then p-toluenesulfonic acid monohydrate (122 mg, 0.64 mmol; Aldrich) was added. After stirring the mixture for 16 hours, the resulting solid was collected by filtration to afford the title compound (245 mg, 0.30 mmol; 94%). 1H NMR (300 MHz, methanol-d4): δ 7.89 (2H, d, J=8 Hz), 7.70 (4H, d, J=8 Hz), 7.47 (2H, d, J=2 Hz), 7.34 (1H, d, J=2 Hz), 7.32 (2H, dd, J=8, 2 Hz), 7.22 (4H, d, J=8 Hz), 5.04 (2H, m), 3.87 (2H, m), 3.5-3.28 (12H, m), 2.55 (2H, m), 2.40-2.21 (7H, m), 2.21-1.83 (5H, m). MS (DCI/NH3): m/z 467 (M+1)+. Anal. Calcd. for C25H30N2O3.2C7H8O3S.0.5H2O: C, 58.59; H, 5.78; N, 3.42. Found: C, 58.58; H, 5.84; N, 3.39.

Workup

  1. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-8becd843665d4b41bf49dbaa8f202716
Source dataset
uspto-grants-2011_05
Patent number
US07951791B2

Reaction notes

Loading…