Propane sultone → HCID 58931799, 화합물

HRID 239780

반응식

HRID 239780 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 58931799HCID 58931799, 화합물수율 89%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1459b54d87904f3f8a56cb1f8a285f68
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642801B2

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