Sodium Carbonate → HCID 9798625, compound

HRID 1940070Notes

Reaction equation

HRID 1940070 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][CH:8]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=1)[CH2:9][C:10]([OH:12])=[O:11].C(N1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38])(OCC)=O>O.C(#N)C>[C:29]1(=[O:38])[N:7]([CH:8]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:17][CH:18]=2)[CH2:9][C:10]([OH:12])=[O:11])[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]12

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 28353093-amino-3-(4-propoxyphenyl)propanoic acid

Product 1

HCID 9798625HCID 9798625, compoundYield 75.2%

Reagents, catalysts & solvents 1

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

Procedure

To a stirred solution of sodium carbonate (1.45 g, 13.7 mmol) in 500 mL of water-acetonitrile (1:1, v/v) was added 3-amino-3-(4-propoxyphenyl)propionic acid (3.05 g, 13.7 mmol) as a solid. The mixture was warmed to 30°-40° C. to dissolve the solids. The reaction mixture was allowed to cool to room temperature and N-carboethoxyphthalimide (3.00 g, 13.7 mmol) was added and the reaction mixture was stirred for one hour at room temperature. The reaction mixture was then partially concentrated to remove the acetonitrile and the pH of the resulting solution was adjusted to approximately 3 with 4N hydrochloric acid. The resulting slurry was stirred overnight and then filtered and the solid was washed with copious amounts of water. The solid was dried in vacuo (60° C., <1 mm) to afford 3.64 g (75%) of 3-phthalimido-3-(4-propoxyphenyl)propionic acid as a white powder: mp 142.5°-143.6° C., 1H NMR(DMSO-6, 250 MHz) δ12.43 (br s, 1H), 7.80-7.95 (m, 4H), 7.34 (d, 2H, J=9 Hz), 6.89 (d, 2H, J=9 Hz), 5.63 (overlapping dd, 1H), 3.88 (t, 2H, J=7 Hz), 3.45 (dd, 1H, J1=9 Hz, J2 =16.5 Hz), 3.30 (dd, 1H, J=7 Hz, J2=16.5 Hz), 1.60-1.85 (m, 2H), 0.95 (t, 3H, J=7 Hz); 13C (DMSO-d6) δ171.8, 167.6, 158.6, 134.7, 131.1, 130.8, 128.3, 123.2, 114.4, 68.9, 49.7, 36.0, 22.0, 10.3; Anal. Calcd. for C20H19NO5. Theoretical: C, 67.98; H, 5.42; N, 3.96. Found: C, 67.90; H, 5.40; N, 4.00.

Workup

  1. temperatureThe mixture was warmed to 30°-40° C.
  2. dissolutionto dissolve the solids
  3. concentrationThe reaction mixture was then partially concentrated
  4. customto remove the acetonitrile
  5. stirringThe resulting slurry was stirred overnight
  6. filtrationfiltered
  7. washthe solid was washed with copious amounts of water
  8. customThe solid was dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-a18b72c9816b4f639858502a37207124
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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