Phthalic Anhydride → HCID 178511801, compound

HRID 866489Notes

Reaction equation

HRID 866489 reaction equation
[NH2:1][C@@H:2]([C:9]([NH:11][OH:12])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[C:13]1(=[O:23])[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>CN(C)C=O.O>[C:16]([C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[C:13]([N:11]([C:9](=[O:10])[C@@H:2]([CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1)[NH2:1])[OH:12])=[O:23])([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 6811Phthalic AnhydrideHCID 178511800HCID 178511800, compound

Product 1

HCID 178511801HCID 178511801, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

D-Histidine hydroxamic acid (1.9 g, 11.2 mMol) was dissolved in dimethylformamide (75 ml) and water (100 ml). Phthalic anhydride (1.65 g, 11.2 mMol) was added, the solution stirred 4 hours, evaporated to an oil which was crystallized from water/ethanol, and crystallized again from water to yield 1.6 g, m.p. 175° (dec.) of N-(2-carboxybenzoyl)-D-histidine hydroxamic acid.

Workup

  1. customevaporated to an oil which
  2. customwas crystallized from water/ethanol
  3. customcrystallized again from water

Sources & evidence

ORD record
ord-e4bf9746559d46508b33f12f3eede311
Source dataset
uspto-grants-1978_07
Patent number
US04099010

Reaction notes

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