Dl-Phenylalanine → N-Phthaloyl-DL-phenylalanine

HRID 1421290Notes

Reaction equation

HRID 1421290 reaction equation
[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(OCC)=O>O>[C:25]1(=[O:34])[N:1]([CH:2]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([OH:12])=[O:11])[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]12

Participants

5

Reactant 3

HCID 994Dl-PhenylalanineHCID 10340Sodium CarbonateHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 227754N-Phthaloyl-DL-phenylalanineYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of d,l-phenylalanine (4.17 g, 25.0 mmol) and sodium carbonate (2.78 g, 26.25 mmol) in 50 mL of water is added N-carboethoxyphthalimide (5.65 g, 25.0 mmol). The resulting slurry is stirred for 1.5 hour and filtered. The pH of the filtrate is adjusted to 1-2 with 4 N hydrochloric acid with stirring. After 20 minutes, the slurry is refiltered and the solid washed with water. The solid is dried in vacuo (60° C.,<1 mm) to afford 5.44 g (74%) of 2-phthalimido-3-phenylpropionic acid as a white powder: mp 165-169° C.; 1H NMR (DMSO-d6, 250 M Hz) δ 12.5(br s, 1H), 7.84(s, 4H), 7.23-7.06 (m, 5H), 5.13 (dd, 1H, J=5.0), 3.26-3.05 (m, 2H); 13C NMR (250 MHz, DMSO-d6)δ 170.0, 167.0, 137.2, 134.8, 130.6, 128.6, 128.2, 126.5, 123.3, 52.8, 3.3.8. Anal. Calculated for C17H13NO4. Theoretical: C, 69.15; H, 4.44; N, 4.74. Found: C, 69.07; H, 4.34; N, 4.78.

Workup

  1. filtrationfiltered
  2. stirringwith stirring
  3. waitAfter 20 minutes
  4. washthe solid washed with water
  5. customThe solid is dried in vacuo (60° C.,<1 mm)

Sources & evidence

ORD record
ord-063377aae8fc4b55b3c069a7dc6c7fdf
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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