Potassium Carbonate → (2S)-Amino(2-chlorophenyl)acetic acid

HRID 2121003Notes

Reaction equation

HRID 2121003 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH:4]([NH:7]C(C1C=CC=CC=1)C1C=CC=CC=1)C#N.[C:25](=[O:28])([O-])[O-:26].[K+].[K+].[OH-].[K+]>Cl>[CH:22]1[CH:21]=[C:3]([C@H:4]([NH2:7])[C:25]([OH:26])=[O:28])[C:2]([Cl:1])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 13521702HCID 13521702, compound

Product 1

HCID 1501937(2S)-Amino(2-chlorophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The above product was dissolved in aqueous hydrochloric acid (6N, 10 ml) and heated at 70° C. for six hours (until exhaustion of the nitrile). The reaction mixture was cooled to room temperature, made basic (pH >10) by addition of solid potassium carbonate, then with aqueous potassium hydroxide (2M, ca. 5 ml). Washing with ether (3×30 mL), followed by titration to pH 6.5 and concentration of the aqueous phase afforded, upon cooling, a white solid, which was recrystallized to afford a near quantitative yield of L-2-chlorophenylglycine. Analysis by HPLC indicated optical purity of >99%.

Workup

  1. washWashing with ether (3×30 mL)
  2. customafforded
  3. temperatureupon cooling
  4. customa white solid, which was recrystallized

Sources & evidence

ORD record
ord-5c882611af4b41769044aee5c7a03a0e
Source dataset
uspto-grants-2004_02
Patent number
US06693168B1

Reaction notes

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