Propane sultone → 3-{[(1r)-1-(Aminocarbonyl)-3-methylbutyl]amino}-1-propanesulfonic acid

HRID 239782

反応式

HRID 239782 の反応式
[NH2:1][C@@H:2]([C:7]([NH2:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH2:10]1[CH2:16][S:13](=[O:15])(=[O:14])[O:12][CH2:11]1>C(#N)C>[NH2:9][C:7]([C@H:2]([NH:1][CH2:11][CH2:10][CH2:16][S:13]([OH:15])(=[O:14])=[O:12])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:8]

参加物

4

反応物 2

HCID 14264Propane sultoneHCID 7271815(R)-2-Amino-4-methylpentanamide

生成物 1

HCID 160361803-{[(1r)-1-(Aminocarbonyl)-3-methylbutyl]amino}-1-propanesulfonic acid収率 74.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of D-Leucinamide (6.0 mmol) in acetonitrile (35 mL) was added 1,3-propanesultone (666 mg, 5.5 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was filtered and washed with MeCN (2×20 mL). The solid was suspended in EtOH (50 mL). The suspension was stirred at reflux for 1 hour. The mixture was cooled to room temperature. The solid material was filtered, washed with acetone (1×20 mL) and dried in a vacuum oven (50° C.), affording the title compound (1.03 g, 74%): 1H NMR (D2O, 500 MHz) δ ppm 3.81 (m, 1H), 3.07 (m, 2H), 2.85 (t, 2H, J=7.3 Hz), 2.03 (m, 2H), 1.68 (t, 1H, J=7.8 Hz), 1.58 (m, 2H), 0.83 (m, 6H). 13C (D2O, 125 MHz) δ ppm 171.45, 59.39, 48.01, 45.41, 39.02, 24.24, 22.21, 21.47, 21.13. [α]D=−13.7° (c=0.0019 in water), ES-MS 251 (M−1).

後処理

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was filtered
  3. washwashed with MeCN (2×20 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 1 hour
  6. temperatureThe mixture was cooled to room temperature
  7. filtrationThe solid material was filtered
  8. washwashed with acetone (1×20 mL)
  9. customdried in a vacuum oven (50° C.)

出典と根拠

ORDレコード
ord-b7f98224b70c4e02adbd92efa028e1a9
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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