Sodium Carbonate → HCID 178525360, compound

HRID 2211254Notes

Reaction equation

HRID 2211254 reaction equation
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])(OCC)=O>O>[C:24]1(=[O:33])[N:1]([CH:2]([CH2:3][C:4]2[N:8]=[CH:7][NH:6][CH:5]=2)[C:9]([OH:11])=[O:10])[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]12

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 178419078HCID 178419078, compound

Product 1

HCID 178525360HCID 178525360, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of histidine (3.17 g, 20.0 mmol) and sodium carbonate (2.23 g, 21 mmol) in 50 mL of water is added N-carboethoxyphthalimide (4.52 g, 20.0 mmol). After 1.5 hour, the reaction slurry is filtered. The filtrate is stirred and the pH adjusted to 1-2 with 4N hydrochloric acid. The resulting slurry is filtered and the solid washed with water and dried in vacuo (60 C, <1 mm) to afford 3.65 g (64%) of 2-phthalimido-3-(imidazol-4-yl)propionic acid as a white powder: mp 280°-285° C.; 1H NMR (dmso-d6, 250 M Hz) δ12.5 (br s, 1H), 7.90-7.60 (m, 6H), 6.80(s, 1H), 4.94 (t, 1H, J=7.8), 3.36 (d, 2H, J=7.8); 13C NMR (dmso-d6) δ 170.1, 167.1, 134.8, 134.6, 133.2, 131.1, 123.2, 116.3, 52.4, 25.8; Anal. Calculated for C14H11N3O4. Theoretical: C, 58.95; H, 3.89; N, 14.73. Found: C, 58.80; H, 3.88; N, 14.66.

Workup

  1. filtrationthe reaction slurry is filtered
  2. filtrationThe resulting slurry is filtered
  3. washthe solid washed with water
  4. customdried in vacuo (60 C, <1 mm)

Sources & evidence

ORD record
ord-c9af4b2be9cb4a29997cfa4229a76b61
Source dataset
uspto-grants-1995_10
Patent number
US05463063

Reaction notes

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