p-Toluenesulfonic acid monohydrate → HCID 86760919, compound

HRID 227373Notes

Reaction equation

HRID 227373 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([C:31]([CH:33]3[C:35]([CH3:37])([CH3:36])[C:34]3([CH3:39])[CH3:38])=[O:32])=[CH:23]2)[CH2:16][CH2:15]1>>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[CH3:13][N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([C:31]([CH:33]3[C:34]([CH3:39])([CH3:38])[C:35]3([CH3:37])[CH3:36])=[O:32])=[CH:23]2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 44626510HCID 44626510, compound

Product 1

HCID 86760919HCID 86760919, compoundYield 12.2%

Procedure

p-Toluenesulfonic acid monohydrate (78 mg, 0.41 mmol) and the product of Example 7A (0.15 g, 0.41 mmol) were processed as in Example 1E. Recrystallization with CH3OH and EtOAc provided 25 mg of the title compound (0.050 mmol, 12% yield). 1H NMR (MeOH-d4, 300 MHz) δ 1.33 (s, 12H), 1.54 (m, 3H), 1.91 (br q, J=7.1 Hz, 2H), 2.03 (m, 2H), 2.15 (s, 1H), 2.81 (s, 3H), 2.93 (m, 2H), 3.26 (m, 1H), 3.45 (m, 2H), 4.34 (t, J=7.1 Hz, 2H), 6.70 (s, 2H), 7.21 (dd, J=7.8, 1.0 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 7.49 (br d, J=8.1 Hz, 1H), 8.09 (s, 1H), 8.25 (br d, J=7.1 Hz, 1H); MS (DCI/NH3) m/z 367 (M+H)+; Anal. Calculated for C24H34N2O.C4H4O4.0.5CH4O: C, 68.65; H, 8.09; N, 5.62. Found: C, 68.68; H, 8.49; N, 5.82.

Workup

  1. customRecrystallization with CH3OH and EtOAc

Sources & evidence

ORD record
ord-d66719352a27459d877c712f4bfd8cfc
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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