Hydrochloric Acid → (R)-2-Acetamido-3-(4-cyanophenyl)propanoic acid

HRID 1899775Notes

Reaction equation

HRID 1899775 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][C@@H:8]([C:13]([OH:15])=[O:14])[NH:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1)#[N:2].Cl.[Cl-].[Na+]>[OH-].[Na+]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C@H:8]([C:13]([OH:15])=[O:14])[NH:9][C:10](=[O:12])[CH3:11])=[CH:16][CH:17]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5234Sodium ChlorideHCID 11085640(S)-2-Acetamido-3-(4-cyanophenyl)propanoic acid

Product 1

HCID 11075272(R)-2-Acetamido-3-(4-cyanophenyl)propanoic acidYield 28.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of DL-4-cyano-N-acetylphenylalanine (114.0 g), cobalt chloride(II) (0.63 g) and acylase Amano 15000 (Trademark) (6.27 g) in 1N sodium hydroxide aqueous solution (492 ml) was adjusted to pH=7.5 with 0.1N hydrochloric acid and 0.1N sodium chloride aqueous solution, and then was stirred at 33°-36° C. for 20 hours. The reaction mixture was adjusted to pH=1 with 10% hydrochloric acid, and was washed with ethyl acetate, and the resulting precipitate was collected by filtration. The precipitate was washed with 10% hydrochloric acid and water to give 4-cyano-N-acetyl-D-phenylalanine (32.00 g).

Workup

  1. washwas washed with ethyl acetate
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThe precipitate was washed with 10% hydrochloric acid and water

Sources & evidence

ORD record
ord-26510d7233b94f689054c09e993f8566
Source dataset
uspto-grants-1996_11
Patent number
US05574016

Reaction notes

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