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

HRID 1284935Notes

Reaction equation

HRID 1284935 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

To an aqueous solution (200 ml) of 1.4 g of sodium carbonate are added 2.9 g of S-(o-nitrophenyl)-L-cysteine and 3.5 g of N-ethoxycarbonylphthalimide. After being stirred at room temperature for 5 hours, the reaction mixture is filtered to remove the insoluble substance, and the filtrate is made weakly acid with concentrated hydrochloric acid. The deposited crystals are collected 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.

Workup

  1. filtrationthe reaction mixture is filtered
  2. customto remove the insoluble substance
  3. filtrationThe deposited crystals are collected by filtration
  4. customrecrystallized from 30 ml of ethanol

Sources & evidence

ORD record
ord-9e5c56f17df8448781e7052dd682f43c
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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