Propane sultone → HCID 58931799、化合物

HRID 239780

反応式

HRID 239780 の反応式
[NH2:1][C@@H:2]([C:10]([NH2:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1>C(#N)C>[C:10]([C@H:2]([NH:1][CH2:14][CH2:13][CH2:19][S:16]([OH:18])(=[O:17])=[O:15])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:11])[NH2:12]

参加物

4

反応物 2

HCID 14264Propane sultoneHCID 7000171(2R)-2-amino-3-phenylpropanamide

生成物 1

HCID 58931799HCID 58931799、化合物収率 89%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of D-Phenylalaninamide (1.83 g, 11.1 mmol) in acetonitrile (20 mL) was added 1,3-propane sultone (1.29 g, 10.6 mmol). The solution was stirred at reflux for 2.5 hours. The reaction mixture was cooled to room temperature. The solid was filtered and washed with acetonitrile (2×20 mL). The solid product was suspended in EtOH (75 mL). The suspension was stirred at reflux for 1 hours. The solid material was filtered, washed with acetone (1×25 mL) and dried in vacuo, affording the title compound (2.62 g, 89%). 1H NMR (D2O, 500 MHz) δ ppm 7.28 (m, 3H), 7.19 (m, 2H), 4.05 (m, 1H), 3.19 (dd, 1H, J=5.3 Hz, 14.2 Hz), 3.04 (m, 3H), 2.86 (t, 2H, J=5.8 Hz), 2.03 (m, 2H). 13C (D2O, 125 MHz) δ ppm 170.39, 133.73, 129.62, 129.26, 128.15, 61.57, 47.99, 45.57, 36.21, 21.45. [α]D=−20.7° (c=0.0038 in water), ES-MS 285 (M−1).

後処理

  1. temperatureat reflux for 2.5 hours
  2. filtrationThe solid was filtered
  3. washwashed with acetonitrile (2×20 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 1 hours
  6. filtrationThe solid material was filtered
  7. washwashed with acetone (1×25 mL)
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-1459b54d87904f3f8a56cb1f8a285f68
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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