(R)-3-(4-FLUOROPHENYL)BUTANOIC ACID synthesis

5synthesis methods

Product Name:(R)-3-(4-FLUOROPHENYL)BUTANOIC ACID
CAS Number:209679-21-0
Molecular formula:C10H11FO2
Molecular Weight:182.19

Benzenepropanoic acid, 4-fluoro-β-methyl-, ethyl ester

162549-00-0
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209679-21-0
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209679-20-9
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Benzenepropanoic acid, 4-fluoro-β-methyl-, ethyl ester, (βR)-

1286204-36-1
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Yield:-

Reaction Conditions:

with Pseudomonas cepacia P₁ hydrolase;water at 30; pH=7; for 64 h;aq. phosphate buffer;Enzymatic reaction;optical yield given as %ee;enantioselective reaction;

Steps:

4.11.1. General procedure for the hydrolase catalysed kinetic resolution of the 3-aryl alkanoic ethyl esters (+/-)-3a-i (analytical scale)

General procedure: A spatula tip of enzyme (5-10 mg) was added to the substrate (+/-)-3a-i (50 mg) in 0.1 M phosphate buffer, pH 7 (4.5 mL). Co-solvents (17% v/v) were added as indicated in Table 3. The reaction vessel was shaken at 700-750 rpm and incubated at the appropriate temperature for the required length of time. The aqueous layer was extracted with diethyl ether (3 × 5 mL) and the combined organic extracts were filtered through Celite and concentrated under reduced pressure. The sample was analysed by ¹H NMR spectroscopy, reconcentrated and dissolved in a mixture of hexane/iso-propyl alcohol (HPLC grade) and enantioselectivity determined by chiral HPLC. The results of the screen are summarised in the appropriate [Table 1] and [Table 10].

References:

Deasy, Rebecca E.;Brossat, Maude;Moody, Thomas S.;Maguire, Anita R. [Tetrahedron Asymmetry,2011,vol. 22,# 1,p. 47 - 61] Location in patent:experimental part

1765-93-1 Synthesis