HCID 10755519, compound → HCID 10657826, compound

HRID 1957773Notes

Reaction equation

HRID 1957773 reaction equation
C([NH:4][CH:5]([CH2:9][C:10]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[NH2:19])=[O:11])[C:6]([OH:8])=[O:7])(=O)C>Cl>[NH2:4][C@H:5]([CH2:9][C:10]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[NH2:19])=[O:11])[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 10755519HCID 10755519, compound

Product 1

HCID 10657826HCID 10657826, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (-)-2-acetamido-4-(2-amino-5-chlorophenyl)-4-oxo-butyric acid (0.76 g, 2.67 mmol) in 2N HCl (90 ml) was heated at reflux temperature for 3 h. The aqueous solution was evaporated to dryness, the residue was dissolved in water, washed with CH2Cl2 and evaporated again. The residue was dissolved in water (30 ml) and adjusted to pH 6.5 with 1N NaOH: a light yellow solid separated. The solid was filtered and washed with cold water to obtain (R)-(+)-2-amino-4-(2-amino-5-chlorophenyl)-4-oxo-butyric acid (0.40 g; 59.7%; m.p. 210°-211° C. (dec.); [α]20D =+11.5 (1%, CH3COOH); ee=96%).

Workup

  1. temperatureat reflux temperature for 3 h
  2. customThe aqueous solution was evaporated to dryness
  3. dissolutionthe residue was dissolved in water
  4. washwashed with CH2Cl2
  5. customevaporated again
  6. dissolutionThe residue was dissolved in water (30 ml)
  7. customa light yellow solid separated
  8. filtrationThe solid was filtered
  9. washwashed with cold water

Sources & evidence

ORD record
ord-57918b16e5ce4c5aac1e51aa3b6d04f1
Source dataset
uspto-grants-1998_07
Patent number
US05786508

Reaction notes

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