N-Carbethoxyphthalimide → 3-(o-nitrophenyl)thio-2(R)-phthalimidopropionic acid

HRID 980587Notes

Reaction equation

HRID 980587 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])([O-:3])=[O:2].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+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@H:12]([N:13]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:14]([OH:16])=[O:15])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 124713S-o-nitrophenyl-L-cysteine

Product 1

HCID 136052823-(o-nitrophenyl)thio-2(R)-phthalimidopropionic acidYield 80.8%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

In an aqueous solution (200 ml) of 1.4 g of sodium carbonate is dissolved 2.9 g of S-(o-nitrophenyl)-L-cysteine, and 3.5 g of N-ethoxycarbonylphthalimide is added to the solution under stirring. After the mixture is stirred at room temperature for 5 hours, the insoluble matter is removed by filtration, and the filtrate is made weakly acid with concentrated hydrochloric acid. The crystals which separate out are recovered by filtration, and recrystallized from 30 ml of ethanol to give 3.6 g of 3-(o-nitrophenyl)thio-2(R)-phthalimidopropionic acid as pale yellow needles, melting at 220°-222° C.

Workup

  1. additionis added to the solution
  2. stirringAfter the mixture is stirred at room temperature for 5 hours
  3. customthe insoluble matter is removed by filtration
  4. customThe crystals which separate out
  5. filtrationare recovered by filtration
  6. customrecrystallized from 30 ml of ethanol

Sources & evidence

ORD record
ord-ccee5d32d41c4c08af11e1808308c8e9
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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