Ammonia → 14182-57-1

HRID 965451Notes

Reaction equation

HRID 965451 reaction equation
[C:1]1([CH:7]([CH3:13])[C:8](OCC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:14]>C(O)(C)(C)C>[C:1]1([C@@H:7]([CH3:13])[C:8]([NH2:14])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 99643Benzeneacetic acid, alpha-methyl-, ethyl ester

Product 1

HCID 1239923414182-57-1Yield 90%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 1.6 g of ethyl 2-phenyl-propionate and 18 ml of tert-butanol is treated at 50° C. with stirring with 0.35 g of lipase from Candida antarctica (Novozym 435, activity 7000 PLU/g). Ammonia is then passed into the reaction mixture with stirring at 50° to 53° C. until it is saturated. The mixture is stirred at 50° to 53° C. for a further 8 hours and during the course of this a slow stream of ammonia is continuously passed through the apparatus. The mixture is then worked up in the manner indicated in Example 1. 0.6 g (90% of theory, conversion 46 area per cent GC) of (R)-2-phenyl-propionamide having an ee value of >98% is obtained.

Workup

  1. additionis treated at 50° C.
  2. stirringwith stirring at 50° to 53° C. until it

Sources & evidence

ORD record
ord-81bfbd9aa187447fa4cfa1a216d56c14
Source dataset
uspto-grants-1998_06
Patent number
US05773656

Reaction notes

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