Sodium Carbonate → methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoate

HRID 1417378노트

반응식

HRID 1417378 반응식
Cl.[CH3:2][O:3][C:4](=[O:14])[CH2:5][CH:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36])(OCC)=O.C(OCC)(=O)C.CCCCCC>O.C(#N)C>[C:27]1(=[O:36])[N:13]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4]([O:3][CH3:2])=[O:14])[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]12

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 2834577Methyl 3-phenyl-3-amino-propionate hydrochlorideHCID 21226206Ethyl acetate hexane

생성물 1

HCID 4461504methyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoate수율 39.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 3-amino-3-phenylpropionic acid methyl ester hydrochloride (0.50 g, 2.3 mmol) and sodium carbonate (0.25 g, 2.3 mmol) in 10 mL of water was added N-carboethoxyphthalimide (0.51 g, 2.3 mmol) in 7 mL of acetonitrile. The reaction progress was monitored by TLC (ethyl acetate/hexane; 1:2) which showed that the reaction was complete in one hour. The reaction mixture was partially concentrated to remove the acetonitrile. The resulting slurry was filtered and the solid was washed with 20 mL of water. The solid was dried in vacuo (60° C., <1 mm) to afford 280 mg (39.4%) of methyl 3-phthalimido-3-phenylpropionate as a white powder: mp 75°-76° C.; 1H NMR (DMSO-d6, 250 MHz) δ 7.26-7.83 (m, 9H), 5.68-5.75 (m, 1H), 3.55 (S, 3H), 3.37-3.66 (m, 2H); 13C NMR (DMSO-d6) δ 170.7, 167.6, 138.6, 134.7, 131.0, 128.6, 127.8, 126.9, 123.3, 51.6, 49.9, 35.3. Anal. Calcd for C18H15NO4 : C, 69.89; H, 4.89; N, 4.53; Found: C, 69.69; H, 4.83; N, 4.49.

후처리

  1. concentrationThe reaction mixture was partially concentrated
  2. customto remove the acetonitrile
  3. filtrationThe resulting slurry was filtered
  4. washthe solid was washed with 20 mL of water
  5. customThe solid was dried in vacuo (60° C., <1 mm)

출처 및 근거

ORD 기록
ord-a6f6349775284fbe8f8e9818711d03f8
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877200

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