Hydrochloric Acid → N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine Benzylester

HRID 1906627Notes

Reaction equation

HRID 1906627 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[C@H:10]([CH3:23])[NH:11][CH:12]([C:21]#N)[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O.C([O-])(O)=[O:28].[Na+].[CH2:32]([OH:34])[CH3:33]>ClCCl.C(#N)C>[CH2:1]([O:8][C:9](=[O:24])[C@H:10]([CH3:23])[NH:11][CH:12]([C:21]([O:34][CH2:32][CH3:33])=[O:28])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 13826599N-(1-Cyano-3-Phenylpropyl)-L-Alanine Benzylester

Product 1

HCID 13345971N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine Benzylester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

N-(1-Cyano-3-Phenylpropyl)-L-Alanine Benzylester (4.24 g) is then dissolved in 65 ml dry dichloromethane and diluted with 2.39 g absolute ethanol. After cooling on ice, the solution is saturated with dry HCl, stored for 2 days at 0°-5° C., and evaporated to form a residue which is dissolved in 30 ml of a 2:1 acetonitrile:water mixture at room temperature for 15 minutes. An excess of aqueous NaHCO3 is then added to the mixture, which is extracted with chloroform several times, dried over MgSO4, and placed under vacuum to evaporate the solvent, yielding N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine Benzylester [TLC (Silica gel; CHCl3 /acetone=9:1); Rf=0.60].

Workup

  1. temperatureAfter cooling on ice
  2. customevaporated
  3. customto form a residue which
  4. extractionis extracted with chloroform several times
  5. dry with materialdried over MgSO4
  6. customto evaporate the solvent

Sources & evidence

ORD record
ord-1baf1110c54740bcadf30185f0d12406
Source dataset
uspto-grants-1987_03
Patent number
US04652668

Reaction notes

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