Sodium Carbonate → HCID 9798625, compound

HRID 1421302Notes

Reaction equation

HRID 1421302 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

Conditions

Temperature
35 °C

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-d6, 250 MHz)δ 12.43 (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, J1=7 Hz, J2=16.5 Hz), 1.60-1.85 (m, 2H), 0.95 (t, 3H, J=7 Hz); 13C (DMSO-d6)δ 171.8, 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. dissolutionto dissolve the solids
  2. temperatureto cool to room temperature
  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-7e5f1811785f46d0b63ed0a0e815e803
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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