N-Carbethoxyphthalimide → 4-(2-Nitrophenyl)-2-phthalimidobutyric acid

HRID 1031813Notes

Reaction equation

HRID 1031813 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])[C:3]([OH:5])=[O:4].C(OC(N1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])=O)C>C(=O)([O-])[O-].[Na+].[Na+]>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][CH2:6][CH:2]([N:1]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])[C:3]([OH:5])=[O:4])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 132435482-Amino-4-(2-nitrophenyl)butyric acid

Product 1

HCID 144072514-(2-Nitrophenyl)-2-phthalimidobutyric acidYield 70.3%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

In an aqueous solution (150 ml) of 6.1 g of sodium carbonate is dissolved 11.7 g of 2-amino-4-(2-nitrophenyl)butyric acid, and 15 g of N-ethoxycarbonylphthalimide is added to the solution under stirring. After stirring at room temperature overnight, the insoluble material is removed by filtration, and the filtrate is made weakly acidic with concentrated hydrochloric acid. The viscous material, which separates out, is admixed with 50 ml of ethanol, followed by stirring, whereby there separate out crystals. The crystals are collected by filtration and dried to give 13 g of 4-(2-nitrophenyl)-2-phtalimidobutyric acid as colorless crystals. m.p. 177°-179° C.

Workup

  1. additionis added to the solution
  2. stirringAfter stirring at room temperature overnight
  3. customthe insoluble material is removed by filtration
  4. stirringby stirring
  5. customwhereby there separate out crystals
  6. filtrationThe crystals are collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-2d85a65d3f954a91b4d545d27e18ef87
Source dataset
uspto-grants-1990_09
Patent number
US04954625

Reaction notes

Loading…