Hydrochloric Acid → HCID 178512481, compound

HRID 363515Notes

Reaction equation

HRID 363515 reaction equation
Cl.[NH:2]([C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[CH2:9][C:10]([NH:17]C(=O)C(CC)CC)(C([O-])=O)[C:11]([O-:13])=[O:12])[C:3]([NH2:5])=[NH:4]>O>[NH:2]([C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[CH2:9][CH:10]([C:11]([OH:13])=[O:12])[NH2:17])[C:3]([NH2:5])=[NH:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178445213HCID 178445213, compound

Product 1

HCID 178512481HCID 178512481, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50% solution of concentrated hydrochloric acid in water (40 mls) was added to 3-guanidino-benzyldiethylacetamidomalonate (910 mg, 2.5 mmol). The reaction mixture was stirred at reflux for 15 hours. The solvent was evaporated to a third of the volume and the crude product purified by ion exchange chromatography (Dowex AG 50W-X8, 100-200 mesh resin, 16 ml wet bed volume), eluting with 0.1M ammonia solution to give a tan glass/oil. Futher purified by flash column chromatography (10% 880 ammonia/methanol) gave 3-guanidino-DL-phenylalanine (240 mg, 43%) as a tan glass.

Workup

  1. temperatureat reflux for 15 hours
  2. customThe solvent was evaporated to a third of the volume
  3. customthe crude product purified by ion exchange chromatography (Dowex AG 50W-X8, 100-200 mesh resin, 16 ml wet bed volume)
  4. washeluting with 0.1M ammonia solution
  5. customto give a tan glass/oil
  6. customFuther purified by flash column chromatography (10% 880 ammonia/methanol)

Sources & evidence

ORD record
ord-236e1b5a8d394c00b67b02529ebe4a04
Source dataset
uspto-grants-1999_02
Patent number
US05874472

Reaction notes

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