Hydrochloric Acid → HCID 54087991, compound

HRID 343943Notes

Reaction equation

HRID 343943 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH:10]1[NH:14]C(=O)N[C:11]1=[O:16].[OH-:17].[Na+].Cl>>[NH2:14][CH:10]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[C:7]([OH:8])[C:2]=1[CH3:1])[C:11]([OH:16])=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70075092HCID 70075092, compound

Product 1

HCID 54087991HCID 54087991, compound

Procedure

A solution of 5-(2-methyl-3,5-dihydroxyphenyl)-hydantoin (400 mg, 1.8 mmol) in 2M sodium hydroxide (4.5 ml, 9 mmol) was heated in a sealed vessel at 110° C. for 48 hours. The reaction mixture was allowed to cool, neutralised with 2M hydrochloric acid and purified by cation-exchange chromatography (Dowex 50×8-100; column eluted sequentially with water,water:THF 1:1 and water again. The amino acid was finally eluted with water:pyridine 9:1). The pyridine was removed in vacuo and the residual solid redissolved in water and freeze-dried to give the title compound as a light brown solid, m.p. 215° C. (dec).

Workup

  1. temperatureto cool
  2. custompurified by cation-exchange chromatography (Dowex 50×8-100
  3. washcolumn eluted sequentially with water,water:THF 1:1 and water again
  4. washThe amino acid was finally eluted with water:pyridine 9:1)
  5. customThe pyridine was removed in vacuo
  6. dissolutionthe residual solid redissolved in water
  7. customfreeze-dried

Sources & evidence

ORD record
ord-176c477b6a854528a74aad08ae4b9069
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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