Ammonia → HCID 11052302, compound

HRID 965450Notes

Reaction equation

HRID 965450 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[NH3:15]>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:14])[C:9]([NH2:15])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10867613HCID 10867613, compound

Product 1

HCID 11052302HCID 11052302, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
-50 °C

Procedure

A mixture of 5 g of racemic ethyl 2-(4-chloro-phenyl)-propionate and 50 ml of tert-butanol is added to an autoclave at room temperature and treated with 1 g of lipase from Candida antarctica (Novozym 435, activity 7000 PLU/g). The mixture is then cooled to -50° C. and 0.5 g of ammonia is condensed into the reaction mixture. The pressure vessel is sealed, warmed to 50° C. and the mixture is allowed to react for 24 hours with stirring. It is then worked up in the manner described above. 1.78 g (42.8% of theory) of (R)-2-(4-chloro-phenyl)-propionamide having an ee value of 99.1% are obtained.

Workup

  1. additionis added to an autoclave at room temperature
  2. additiontreated with 1 g of lipase from Candida antarctica (Novozym 435, activity 7000 PLU/g)
  3. customcondensed into the reaction mixture
  4. customThe pressure vessel is sealed
  5. temperaturewarmed to 50° C.
  6. customto react for 24 hours

Sources & evidence

ORD record
ord-943d3fa89e094fd88e7d9c9b256e896b
Source dataset
uspto-grants-1998_06
Patent number
US05773656

Reaction notes

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