Propane sultone → 3-[(1r,2s)-2-Methylcyclohexyl]amino-1-propanesulfonic acid

HRID 239738

反応式

HRID 239738 の反応式
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH2:8].[CH2:9]1[CH2:15][S:12](=[O:14])(=[O:13])[O:11][CH2:10]1>O1CCCC1>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][CH2:10][CH2:9][CH2:15][S:12]([OH:14])(=[O:13])=[O:11]

参加物

4

反応物 2

HCID 14264Propane sultoneHCID 234322-Methylcyclohexylamine

生成物 1

HCID 117364843-[(1r,2s)-2-Methylcyclohexyl]amino-1-propanesulfonic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-methylcyclohexylamine (98% cis and trans isomers, 10.0 g, 88.3 mmol) in tetrahydrofuran (60 mL) was slowly added a solution of 1,3-propane sultone (10.5 g, 84.1 mmol) in THF (20 mL). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, washed with acetone (2×50 mL). The solid was dissolved in 50% EtOH/water (200 mL); and solution was treated with Dowex 50WX8 resin (15 g). The suspension stirred at room temperature for 15 min. The resin was removed by filtration. The filtrate was concentrated to half of the original volume on a rotary evaporator. The solid product slowly crystallized. The product was collected by filtration, washed with acetone (2×50 mL) and dried in a vacuum oven (50° C.), to afford compound DJ (10.4 g, 53%): 1H NMR (D2O, 500 MHz) δ ppm 3.15 (m, 1H), 3.03 (m, 1H), 2.88 (t, 2H, J=7.3 Hz), 2.76 (m, 1H), 1.98 (m, 3H), 1.68 (m, 2H), 1.51 (m, 2H), 1.18 (m, 3H), 1.01 (m, 1H), 0.92 (m, 3H). 13C NMR (D2O, 125 MHz) δ ppm 62.97, 48.16, 42.72, 34.77, 33.50, 27.57, 24.51, 24.23, 21.51, 17.80. ES-MS 234 (M−1).

後処理

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid material was collected by filtration
  3. washwashed with acetone (2×50 mL)
  4. dissolutionThe solid was dissolved in 50% EtOH/water (200 mL)
  5. additionand solution was treated with Dowex 50WX8 resin (15 g)
  6. stirringThe suspension stirred at room temperature for 15 min
  7. customThe resin was removed by filtration
  8. concentrationThe filtrate was concentrated to half of the original volume on a rotary evaporator
  9. customThe solid product slowly crystallized
  10. filtrationThe product was collected by filtration
  11. washwashed with acetone (2×50 mL)
  12. customdried in a vacuum oven (50° C.)
  13. customto afford compound DJ (10.4 g, 53%)

出典と根拠

ORDレコード
ord-3e36d47d40524405892863bbe9a2764f
出典データセット
uspto-grants-2014_02
特許番号
US08642801B2

関連ノート

読み込み中…