N-(1-phenylethyl)acetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic anhydride (38.4 g) was dropwise added to a solution (200 ml) of (R)-(+)-1-phenylethylamine (30 g) in chloroform under ice-cooling. After completion of the reaction, ice water was added thereto and the mixture was extracted with chloroform. The extract was washed with 1N aqueous solution of sodium hydroxide and water. After drying, the mixture was concentrated under reduced pressure to give crystals, which were recrystallized from isopropyl ether to give 32.2 g of (+)-N-(1-phenylethyl)acetamide. [α]D =+143.5° (ethanol, c=1) cooling was added the mixture was extracted with chloroform The extract was washed with 1N aqueous solution of sodium hydroxide and water After drying the mixture was concentrated under reduced pressure to give crystals, which were recrystallized from isopropyl ether

Conditions: temp:28.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. fermenter filled with 20 l of basic medium is prepared

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 1 g (6.13 mmol) racemic N-acetyl 1-phenylethylamine (+/−)-1a, partially dissolved in 100 ml 0.1 M phosphate buffer pH 7.0, 100 ml (25.3 units) acylase from Arthrobacter aurescens Ac5R is added and the mixture is shaken (100 rpm) at 20° C. for 27 hours. After acidification (pH 2) by addition of HCl the reaction mixture is extracted three times with 100 ml dichloromethane. The combined organic layers are dried (MgSO4) and the solvent is distilled off after filtration, yielding 0.496 g (49.6%) of (S)-N-acetyl 1-phenylethylamine (−)-1a ([α]D20=−138.0° (c=1.0 EtOH), enantiomeric ratio S/R=96.8:3.2) as a white solid. The aqueous phase is neutralized by addition of NaHCO3 and extracted again with dichloromethane. Usual workup leads to 0.323 g (43.5%) of (R)-1-phenylethylamine (+)-1b ([α]D20=+29.4° (c=2.2 EtOH), enantiomeric ratio R/S=99.7:0.3) as colorless oil. is added is extracted three times with 100 ml dichloromethane The combined organic layers are dried (MgSO4) the solvent is distilled off after filtration

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(1-phenylethyl)acetamide (5.0 g) in dichloromethane (100 ml) was added dropwise titanium tetrachloride (16.7 ml) at below 5° C. over 30 min. Thereto was added dropwise a solution of dichloromethyl methyl ether (14.1 ml) in dichloromethane (30 ml) solution at below 5° C. over 30 min. The mixture was stirred at 25° C. for 3 hr, at room temperature for 12 hr, and then at 25° C. for 3 hr, and poured into ice water (800 ml) and extracted with ethyl acetate. The extract was washed successively with a saturated sodium hydrogencarbonate solution (500 ml) and saturated brine (500 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=1:3) to give the title compound (0.35 g) as a colorless oil. at 25° C. for 3 hr extracted with ethyl acetate The extract was washed successively with a saturated sodium hydrogencarbonate solution (500 ml) and saturated brine (500 ml) dried over anhydrous sodium sulfate The solvent was evaporated the obtained residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=1:3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-phenylethylamine (10.45 g) and triethylamine (14.4 ml) in dichloromethane (100 ml) was added dropwise acetic anhydride (9.0 ml) at room temperature. The mixture was stirred at room temperature for 5 hr. The reaction mixture was poured into ice water (200 ml) and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was left standing at room temperature for 3 hr. The obtained crude crystals were washed several times with hexane to give the title compound (14.0 g) as white crystals. extracted with chloroform The organic layer was dried over anhydrous sodium sulfate the solvent was evaporated The obtained residue was left standing at room temperature for 3 hr The obtained crude crystals were washed several times with hexane