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

HRID 1421298Notes

Reaction equation

HRID 1421298 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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 vas 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.

Workup

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

Sources & evidence

ORD record
ord-fa14b2ca9f1747e98cb00a071df71a6d
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

Loading…