2-Acetamido-5-phenylpentanoic acid → 2-Amino-5-phenylpentanoic acid

HRID 378926Notes

Reaction equation

HRID 378926 reaction equation
C([NH:4][CH:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([OH:8])=[O:7])(=O)C>Cl.O>[NH2:4][CH:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 2279462-Acetamido-5-phenylpentanoic acid

Product 1

HCID 2968662-Amino-5-phenylpentanoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A stirred suspension of (±)-2-(acetylamino)-5-phenyl-pentanoic acid (0.5003 g, 0.002126 mol) in 2.8 M hydrochloric acid was refluxed for 2 hours, and the resulting brown solution was allowed to cool. A tan precipitate formed upon cooling. The solids were filtered off, and the filtrate was rotary evaporated to give a yellow gum. The gum was dissolved in hot water, gravity filtered, and allowed to cool. The mixture was made basic with 1 M sodium hydroxide to pH=5. The resulting precipitate was filtered off, washed with water, and dried in vacuo to give a yellow solid; yield 0.205 g (50%), mp=213-215° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureto cool
  3. customA tan precipitate formed
  4. temperatureupon cooling
  5. filtrationThe solids were filtered off
  6. customthe filtrate was rotary evaporated
  7. customto give a yellow gum
  8. filtrationgravity filtered
  9. temperatureto cool
  10. filtrationThe resulting precipitate was filtered off
  11. washwashed with water
  12. customdried in vacuo
  13. customto give a yellow solid

Sources & evidence

ORD record
ord-175496a9e675424fb66852065d8ddadf
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

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