Sodium Carbonate → HCID 9927069, compound

HRID 1940063Notes

Reaction equation

HRID 1940063 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].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:27]1(=[O:36])[N:1]([CH:2]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=2)[CH2:3][C:4]([OH:6])=[O:5])[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]12

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 35887523-amino-3-(4-cyanophenyl)propanoic acid

Product 1

HCID 9927069HCID 9927069, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 3-amino-3-(4-cyanophenyl)propionic acid (3.80 g, 20.0 mmol) and sodium carbonate (2.23 g, 21 mmol) in 100 mL of water is added N-carboethoxyphthalimide (4.52 g, 20.0 mmol). After 2 hour, the reaction slurry is filtered and the pH of the stirred filtrate adjusted to 1-2 with 4N hydrochloric acid. The resulting gel is extracted with ethyl acetate (3×30 mL). The extract is dried over magnesium sulfate and concentrated in vacuo. The crude product is recrystallized from 10% aqueous acetonitrile and then recrystallized from 20% aqueous methanol. The product is dried in vacuo (60° C., <1 mm) to afford 1.5 g (23%) of 3-phthalimido-3-(4-cyanophenyl)propionic acid as a white powder: mp 134°-137° C.; 1H NMR (DMSO-6, 250 MHz) δ12.5 (br s, 1H), 7.95-7.56 (m, 8H),.5.76 (t, 1H, J=7.7), 3.57-3.15 (m, 2H); 13C NMR (DMSO-d6) δ171.5, 167.6, 144.2, 134.8, 132.6, 131.1, 128.1, 123.3, 118.5, 49.7, 35.5.

Workup

  1. filtrationthe reaction slurry is filtered
  2. extractionThe resulting gel is extracted with ethyl acetate (3×30 mL)
  3. dry with materialThe extract is dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product is recrystallized from 10% aqueous acetonitrile
  6. customrecrystallized from 20% aqueous methanol
  7. customThe product is dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-df1eefae2d3644baab57527d7152cbd1
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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