4-Bromophthalic anhydride → 5-bromo-2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-isoindole-1,3-dione

HRID 331615노트

반응식

HRID 331615 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.Br.[NH2:14][C@@:15]1([CH3:23])[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C:16]1=[O:22].C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:8])[N:14]([C@@:15]1([CH3:23])[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C:16]1=[O:22])[C:9]2=[O:10]

참가 물질

5

반응물 3

HCID 665904-Bromophthalic anhydrideHCID 517045Sodium AcetateHCID 66643102(S)-3-amino-3-methylpiperidine-2,6-dione hydrobromide

생성물 1

HCID 690476895-bromo-2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-isoindole-1,3-dione수율 54%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 4-bromophthalic anhydride (7.53 g, 33.2 mmol), (3S)-3-amino-3-methyl-piperidine-2,6-dione hydrobromide (8.00 g, 44.1 mmol) and sodium acetate (2.72 g, 33.2 mmol) in acetic acid (150 mL) was heated to reflux for 24 hours. The reaction mixture was cooled to room temperature, and the solvent was evaporated under vacuum. The residue was stirred in water (170 mL) for 3 hours, and the resulting solid was filtered, washed with additional water (80 mL), and dried, to afford 6.3 g of 5-bromo-2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-isoindole-1,3-dione, in 54% yield; 1H NMR (DMSO-d6) δ 1.89 (s, 3H), 2.01-2.09 (m, 1H), 2.53-2.73 (m, 3H), 7.79 (dd, J=5.7 Hz, J=2.7 Hz, 1H), 8.06 (m, 2H), 11.04 (s, 1H); 13C NMR (DMSO-d6) δ 21.0, 28.5, 29.0, 58.9, 124.9, 125.9, 128.3, 130.0, 133.0, 137.4, 166.6, 167.2, 172.0, 172.1.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. customthe solvent was evaporated under vacuum
  4. filtrationthe resulting solid was filtered
  5. washwashed with additional water (80 mL)
  6. customdried

출처 및 근거

ORD 기록
ord-e1271c84471a4e0d8054ee70a31721f9
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877780B2

반응 노트

불러오는 중…