Sodium Carbonate → HCID 3121010, compound

HRID 1531859Notes

Reaction equation

HRID 1531859 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[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>C(#N)C.O>[C:27]1(=[O:36])[N:1]([CH:2]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[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 5858893-Amino-3-(4-methoxyphenyl)propanoic acid

Product 1

HCID 3121010HCID 3121010, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a stirred mixture of 3-amino-3-(4-methoxyphenyl)propionic acid (1.95 g, 10.0 mmol) and sodium carbonate (1.11 g, 10.5 mmol) in 200 mL of acetonitrile-water 1:1 is added N-carboethoxyphthalimide (2.26 g, 10.0 mmol). After 1 hour, the reaction slurry is filtered. The filtrate is concentrated to remove the acetonitrile and the pH adjusted to 1-2 with 4 N hydrochloric acid and stirred over night. The resulting slurry is filtered and the solid washed with water. The solid is dried in vacuo (60 C, <1 mm) to afford 2.82 g (87%) of 3-phthalimido-3-(4-methoxyphenyl)propionic acid as a white powder: mp 160-164° C.; 1H NMR (DMSO-d6, 250 MHz) δ12.5 (br s, 1H), 7.95-7.80 (m, 4H), 7.36 (d 2H, J=8.7), 6.92 (d, 2H, J=8.4 Hz), 5.18-5.10 (m, 1H), 3.70-3.15 (m, 2H); 13C NMR (DMSO-d6) δ171.7, 167.6, 158.6, 134.6, 131.0, 130.8, 128.3, 123.1, 113.9, 55.0, 49.6, 35.9. Anal. Calculated for C18H15NO5. Theoretical: C, 66.46; H, 4.63; N, 4.31. Found: C, 66.25; H, 4.65; N, 4.28.

Workup

  1. filtrationthe reaction slurry is filtered
  2. concentrationThe filtrate is concentrated
  3. customto remove the acetonitrile
  4. filtrationThe resulting slurry is filtered
  5. washthe solid washed with water
  6. customThe solid is dried in vacuo (60 C, <1 mm)

Sources & evidence

ORD record
ord-90b57e3ec24c406eae1f2d1ff0858bd0
Source dataset
uspto-grants-2001_03
Patent number
US06200987B1

Reaction notes

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