p-Toluenesulfonic acid monohydrate → 2-(5-Methoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole

HRID 2214003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214003
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:27]COC)=[C:7]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:12]=3[N:13]=2)[CH:8]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([OH:27])=[C:7]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:12]=3[N:13]=2)[CH:8]=1

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 219593142-(5-Methoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole

Produkt 1

HCID 1357441682-(5-Methoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazoleAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethyl-benzoxazole (F16) (283 mg, 0.70 mmol) and p-toluenesulfonic acid monohydrate (532 mg, 2.8 mmol) in methanol (20 mL) was stirred overnight at room temperature. After the solvent was removed by evaporation, ethyl acetate (20 mL) was added to the resulting residue, neutralized by Na2CO3, washed with brine and water, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized from hot ethanol/hexane to afford the objective compound as a pale yellow crystal (244 mg, 96%); 1H-NMR (500 MHz, CDCl3) δ3.86 (s, 3H), 4.01 (s, 2H), 4.21 (s, 2H), 7.05 (br s, 2H), 7.17 (dd, 1H, J=7.5, 4.5 Hz), 7.33–7.37 (m, 2H), 7.41 (d, 1H, J=7.5 Hz), 7.48–7.51 (m, 2H), 7.66 (t, 1H, J=7.5 Hz), 8.59 (d, 1H, J=4.5 Hz), 11.00 (s, 1H).

Aufarbeitung

  1. customAfter the solvent was removed by evaporation, ethyl acetate (20 mL)
  2. additionwas added to the resulting residue
  3. washwashed with brine and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from hot ethanol/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8702f15b3d404fdca2a05da499e7f836
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105680B1

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