Hydrochloric Acid → N-phthaloyl-L-glutamic acid

HRID 364215Notes

Reaction equation

HRID 364215 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:11]([C:16]1[CH:26]=[CH:25][CH:24]=[C:18]2C(N[C:22](=[O:23])[C:17]=12)=O)(OCC)=[O:12].Cl>C([O-])([O-])=O.[Na+].[Na+].O>[CH:25]1[CH:26]=[C:16]2[C:11]([N:1]([C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C:22](=[O:23])[C:17]2=[CH:18][CH:24]=1)=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 33032L-Glutamic AcidHCID 22254400Ethoxycarbonylphthalimide

Product 1

HCID 160453N-phthaloyl-L-glutamic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

In a solution of Na2CO3 (51.5 g) in water (350 ml) at 5° C. was dissolved L-glutamic acid (29.4 g). Carboethoxy phthalimide (59.6 g) was added to the solution and suspended therein and thereafter reacted at 350° C. for 30-40 minutes. Then the solution was freed from insoluble matter, adjusted to pH 2.5 with 6N-HCl, and allowed to stand at 0° C. The resulting precipitate was filtered, and recrystallized from water to give N,N-phthaloylglutamic acid, yield 35.7 g, 64.4%; specific rotation [α]D25 =-48.6° (C=1, dioxane).

Workup

  1. customreacted at 350° C. for 30-40 minutes
  2. customto stand at 0° C
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized from water

Sources & evidence

ORD record
ord-080734b284b144d79f895f368eae62e5
Source dataset
uspto-grants-1986_08
Patent number
US04604451

Reaction notes

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