Propane sultone → 3-{[(1R)-1-(aminocarbonyl)-2-methylpropyl]amino}1-propanesulfonic acid

HRID 239779

反応式

HRID 239779 の反応式
[NH2:1][C@@H:2]([C:6]([NH2:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH2:9]1[CH2:15][S:12](=[O:14])(=[O:13])[O:11][CH2:10]1>C(#N)C>[NH2:8][C:6]([C@H:2]([NH:1][CH2:10][CH2:9][CH2:15][S:12]([OH:14])(=[O:13])=[O:11])[CH:3]([CH3:5])[CH3:4])=[O:7]

参加物

4

反応物 2

HCID 14264Propane sultoneHCID 444079(R)-2-amino-3-methylbutanamide

生成物 1

HCID 160361793-{[(1R)-1-(aminocarbonyl)-2-methylpropyl]amino}1-propanesulfonic acid収率 51%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of D-valinamide (1.76 g, 14.7 mmol) in acetonitrile (30 mL) was slowly added 1,3-propanesultone (1.75 g, 14.4 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with acetonitrile (2×25 mL). The solid product was dissolved in water (75 mL). Dowex Marathon C resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure. The solid material was suspended in acetone (50 mL), filtered and dried in vacuo, affording the title compound (1.57 g, 51%). 1H NMR (D2O, 500 MHz) δ ppm 3.80 (m, 1H), 3.19 (m, 2H), 3.00 (m, 2H), 2.25 (m, 1H), 2.16 (m, 2H), 1.08 (d, 3H, J=6.8 Hz), 1.02 (d, 3H, J=6.8 Hz). 13C (D2O, 125 MHz) δ ppm 169.94, 65.86, 48.10, 46.27, 29.54, 21.23, 17.99, 17.02. [α]D=−12.4° (c=0.0037 in water), ES-MS 237 (M−1).

後処理

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetonitrile (2×25 mL)
  4. dissolutionThe solid product was dissolved in water (75 mL)
  5. additionDowex Marathon C resin (strongly acidic) was added to the solution
  6. stirringThe suspension was stirred for 15 minutes before the resin
  7. customwas removed by filtration
  8. customThe filtrate was evaporated under reduced pressure
  9. filtrationfiltered
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-c3eb7f52c8e7413f8ebba8dd6edd4db6
出典データセット
uspto-grants-2014_02
特許番号
US08642801B2

関連ノート

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