Propane sultone → HCID 16036056, 화합물

HRID 239765노트

반응식

HRID 239765 반응식
[CH2:1]([O:8][C:9](=[O:15])[C@H:10]([CH:12]([CH3:14])[CH3:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]1[CH2:22][S:19](=[O:21])(=[O:20])[O:18][CH2:17]1>CO>[CH2:1]([O:8][C:9]([C@@H:10]([NH:11][CH2:17][CH2:16][CH2:22][S:19]([OH:21])(=[O:20])=[O:18])[CH:12]([CH3:13])[CH3:14])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 14264Propane sultoneHCID 6950584benzyl (2S)-2-amino-3-methylbutanoate

생성물 1

HCID 16036056HCID 16036056, 화합물수율 39%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of L-valine benzylester in MeOH (12 mL) was slowly added 1,3-propanesultone (604 mg, 5.0 mmol). The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with cold MeOH and acetone (2×25 mL). It was dried in the vacuum oven (50° C.), affording the title compound (649 mg, 39%). 1H NMR (D2O, 500 MHz) δ ppm 7.47 (m, 5H), 5.41 (d, 1H, J=11.7 Hz), 5.31 (d, 3H, J=11.7 Hz), 4.04 (m, 1H), 3.19 (m, 2H), 2.95 (t, 2H, J=6.8 Hz), 2.35 (m, 1H), 2.14 (m, 2H), 1.04 (d, 3H, J=6.3 Hz), 0.95 (d, 3H, J=6.3 Hz). 13C (D2O, 125 MHz) δ ppm 168.75, 134.81, 129.38, 129.31, 129.17, 69.00, 65.96, 48.24, 46.71, 29.67, 21.40, 18.39, 16.65. [α]D=−7.2° (c=0.0015 in water), ES-MS 330 (M+1).

후처리

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with cold MeOH and acetone (2×25 mL)
  4. customIt was dried in the vacuum oven (50° C.)

출처 및 근거

ORD 기록
ord-b7cb7d3565354a61b7d473d29ea0faa9
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642801B2

반응 노트

불러오는 중…