Sodium Carbonate → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid

HRID 1264543Notes

Reaction equation

HRID 1264543 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[CH2:14])[C:3]([OH:5])=[O:4].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>[O:31]=[C:30]1[C:29]2[C:28](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27](=[O:36])[N:1]1[CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[CH2:14])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 186125152-Amino-3-(2-vinylphenyl)propanoic acid

Product 1

HCID 186125162-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acidYield 60.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve 2-amino-3-(2-vinyl-phenyl)-propionic acid (3.40 g) in water (75 mL) and add sodium carbonate (1.97 g, 18.6 mmol) and N-carbethoxyphthalimide (2.81 g, 12.8 mmol). Stir for 2.5 hours, wash with methylene chloride (200 mL), acidify to pH 1 with cold concentrated hydrochloric acid and extract with ethyl acetate (3×200 mL), dry (Na2SO4), evaporate the solvent in vacuo and purify by silica gel chromatography (1:1:0.02 hexane/ethyl acetate/acetic acid) followed by recrystallization (isopropanol) to give 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid as a pale yellow solid (2.47 g).

Workup

  1. washwash with methylene chloride (200 mL)
  2. extractionextract with ethyl acetate (3×200 mL)
  3. dry with materialdry (Na2SO4)
  4. customevaporate the solvent in vacuo
  5. custompurify by silica gel chromatography (1:1:0.02 hexane/ethyl acetate/acetic acid)
  6. customfollowed by recrystallization (isopropanol)

Sources & evidence

ORD record
ord-dd22a0a7524445ee8677833f51e826ff
Source dataset
uspto-grants-2003_04
Patent number
US06544980B2

Reaction notes

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