ChemicalBook CAS DataBase List AC-PHE-OME

AC-PHE-OME synthesis

14synthesis methods

Product Name:AC-PHE-OME
CAS Number:3618-96-0
Molecular formula:C12H15NO3
Molecular Weight:221.25

2-Propenoic acid, 2-(acetylamino)-3-phenyl-, methyl ester, (2E)-

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3618-96-0
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Yield:3618-96-0 100%

Reaction Conditions:

with hydrogen;bis(norbornadiene)rhodium(l)tetrafluoroborate;(S)Fc-α-S(C5H5)Fe(C5H3(PPh2)CH(OH)C6H4(PPh2)) in methanol at 25; under 787.579 Torr; for 1 h;Product distribution / selectivity;

Steps:

D.1

0.555 g (2.53 mmol) of methyl trans-acetamidocinnamate and 5 ml of degassed methanol are introduced in succession into a Schlenk vessel filled with argon. A catalyst solution consisting of 4.73 g (0.01265 mmol) of [Rh(norbomadiene)2]BF4, 8.77 mg (0.0133 mmol) of ligand A and 5 ml of degassed methanol is prepared in a second Schlenk vessel filled with argon. This solution and the catalyst solution are then transferred in succession by means of a steel capillary into a 50 ml glass reactor filled with argon. The ratio of substrate/catalyst (s/c) is 200. The reactor is closed and a pressure of 1.05 bar is set by means of 4 flushing cycles (pressurization to 1 bar of hydrogen). The autoclave is thermostated at 25°C and the reaction is started by switching on the stirrer. The reactor is stirred for 1 hour. After opening the reactor, a reddish reaction solution is isolated. The conversion is quantitative (determined by means of GC and 1H-NMR). Removal of the solvent on a rotary evaporator gives a quantitative yield of the methyl ester of (S)-N-acetylphenylalanine having an enantiomeric purity of 99.1% ee (determined by means of GC; column: Chirasil-L-Val.).

References:

WO2005/108409,2005,A2 Location in patent:Page/Page column 30