Diethyl Ether → HCID 86597314, compound

HRID 747930Notes

Reaction equation

HRID 747930 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:16][CH:15]3[CH:11]([CH2:12][N:13]([CH3:17])[CH2:14]3)[CH2:10]2)[CH:6]=[CH:5][C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([OH:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1.C(OCC)C>CCO.CCOC(C)=O>[C:24]1([CH3:34])[CH:25]=[CH:26][C:27]([S:30]([OH:33])(=[O:31])=[O:32])=[CH:28][CH:29]=1.[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:10][CH:11]3[CH:15]([CH2:14][N:13]([CH3:17])[CH2:12]3)[CH2:16]2)[CH:6]=[CH:5][C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 11243775HCID 11243775, compound

Product 1

HCID 86597314HCID 86597314, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To the product of Example 283A (69 mg, 0.224 mmol) in 3 mL 10% EtOH in EtOAc was added p-toluenesulfonic acid (p-TsOH·H2O, 45 mg, 0.24 mmol) in 2 mL 10% EtOH in EtOAc. Diethyl ether (1 mL) was added and the mixture stirred at ambient temperature until a precipitate formed. Filtration yielded 28 mg of the title compound (0.043 mmol, 19% yield). 1H NMR (CH3OH-d4, 300 MHz) δ 2.35 (s, 6H), 2.92 and 2.98 (rotamer s, 3H), 3.19 (m, 3H) 3.38 (m, 3H), 3.63 (m, 3H), 3.77 (s, 3H), 3.98 (m, 1H), 6.50 (m, 1H), 6.52 (s, 1H), 7.16 (m, 1H), 7.22 (m, 5H), 7.32 (m, 2H), 7.42 (m, 2H), 7.70 (m, 4H); MS (DCl/NH3) m/z 309 (M+H)+; Anal. calculated for C20H24N2O·2C7H8O3S: C, 62.55; H, 6.18; N, 4.29; Found: C, 62.17; H, 5.95; N, 4.18.

Workup

  1. customformed
  2. filtrationFiltration

Sources & evidence

ORD record
ord-83220a29184b43df8abb789b35881440
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Reaction notes

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