Potassium Phosphate, Tribasic → (s)-2-Amino-1(4-chlorophenyl)-4-pentene

HRID 1977568Notes

Reaction equation

HRID 1977568 reaction equation
C(NC(C1C=CC=CC=1)C)(=O)C.C([NH:16][CH:17]([CH2:26][CH:27]=[CH2:28])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(=O)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CO>[NH2:16][C@@H:17]([CH2:26][CH:27]=[CH2:28])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 222023N-(1-phenylethyl)acetamideHCID 21993384Racemic 2-acetylamino-1(4-chlorophenyl)-4-pentene

Product 1

HCID 53642805(s)-2-Amino-1(4-chlorophenyl)-4-pentene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
28 °C

Procedure

Strain K1/1 is grown according to example 3 in a 30 l fermenter filled with 20 l of basic medium containing 1 g/l of racemic N-acetyl-1-phenylethylamine. The cells are harvested by continuous centrifugation and resuspended in the reaction mixture, which is prepared by adding a solution of 80 g racemic 2-acetylamino-1(4-chlorophenyl)-4-pentene in 500 ml methanol to 20 l of potassium phosphate buffer, 69 mM, pH 7. After stirring for 21 h at 28° C. and 500 rpm the amine formed and the unreacted amide are separated and analyzed for their optical purity analogously to the procedure given in example 30.

Workup

  1. additionfermenter filled with 20 l of basic medium
  2. customis prepared

Sources & evidence

ORD record
ord-4af2375b94a64d7f80ff7f6842f9a99d
Source dataset
uspto-grants-2001_05
Patent number
US06235516B1

Reaction notes

Loading…