DL-beta-Phenylalanine → 3-(4-Methylphthalimido)-3-phenylpropionic acid

HRID 1531873

반응식

HRID 1531873 반응식
[CH3:1][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.[NH2:13][CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:15][C:16]([OH:18])=[O:17]>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:13]([CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][C:16]([OH:18])=[O:17])[C:6](=[O:8])[C:5]2=[CH:11][CH:12]=1

참가 물질

4

반응물 2

HCID 69189DL-beta-PhenylalanineHCID 880694-Methylphthalic anhydride

생성물 1

HCID 212509643-(4-Methylphthalimido)-3-phenylpropionic acid수율 55%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A stirred mixture of 4-methylphthalic acid anhydride (1.62 g, 10.0 mmol) and 3-amino-3-phenylpropionic acid (1.65 g, 10.0 mmol) in 15 mL of acetic acid under nitrogen was heated to reflux for 6 hours. The resulting reaction solution was concentrated in vacuo to an oil which was crystallized from 20 mL of a 1/1 mixture of ethyl acetate/hexane to afford 1.69 g (55%) of 3-(4-methylphthalimido)-3-phenylpropionic acid as an off-white powder: 1H NMR (DMSO-d6) δ12.5 (br s, 1H, COOH), 7.85-7.55 (m, 3 H, Ar), 7.55-7.2 (m, 5H, Ar), 5.68 (dd, 1H, J=9, 7 Hz, CH), 3.51 (dd, 1H, J=9, 16.5 Hz), 3.29 (dd, 1H, J=9, 16.5 Hz), 2.47 (s, 3H, CH3). Anal. Calcd for C18H15N104. Theory; C, 69.89, H, 4.89, N, 4.53. Found: C, 69.45, H, 4.93, N, 4.55. HPLC: 95%.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. customThe resulting reaction solution
  4. concentrationwas concentrated in vacuo to an oil which
  5. customwas crystallized from 20 mL of a 1/1 mixture of ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-432da2e47bd4427e86e0c3fe1948f4d8
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06200987B1

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