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

HRID 1531863Notes

Reaction equation

HRID 1531863 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>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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 2834577Methyl 3-phenyl-3-amino-propionate hydrochloride

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 acetatethexane; 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) δ7.26-7.83 (m, 9H), 5.68-5.75 (m, 1H), 3.55 (S, 3H), 3.37-3.66 (m, 2H); 13C NMR (DMSO-d6) δ170.7, 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 was washed with 20 mL of water
  5. customThe solid was dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-b4dfb836673f49cfa4704e1b585bc4b8
Source dataset
uspto-grants-2001_03
Patent number
US06200987B1

Reaction notes

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