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

HRID 2214003ノート

反応式

HRID 2214003 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 1357441682-(5-Methoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole収率 96.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8702f15b3d404fdca2a05da499e7f836
出典データセット
uspto-grants-2006_09
特許番号
US07105680B1

反応ノート

読み込み中…