chloramphenicol 3-acetate synthesis
- Product Name:chloramphenicol 3-acetate
- CAS Number:10318-16-8
- Molecular formula:C13H14Cl2N2O6
- Molecular Weight:365.17
108-05-4
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10318-16-8
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Yield: 90%
Reaction Conditions:
with Novozym 435 in acetonitrile at 20; for 3 h;Inert atmosphere;Enzymatic reaction;regioselective reaction;
Steps:
General procedure for the esterification reaction of (-)-chloramphenicol at 0.15 M substrate concentration
General procedure: To a suspension of (-)-chloramphenicol (1, 100 mg, 0.301 mmol) and the corresponding enzyme (CAL-B or PSL, ratio 1:1 in weight respecting 1) in dry solvent (MeCN or 1,4-dioxane, 2.0 mL), the corresponding vinyl ester 3a-f (5 equiv., 1.505 mmol) was added under nitrogen atmosphere. The reaction was shaken at 20 or 30 °C and 250 rpm, and aliquots were regularly analysed by HPLC. The reaction was stopped after complete consumption of the starting material, and then the enzyme was filtered off and washed with EtOAc (3 x 10 mL). Finally the solvent was evaporated under reduced pressure, and the reaction crude purified by flash chromatography on silica gel using mixtures of EtOAc/hexane to afford the desired ester (2'R,3'R)-2a-f.
References:
Bizerra, Ayla M.C.;Montenegro, Tasso G.C.;Lemos, Telma L.G.;De Oliveira, Maria C.F.;De Mattos, Marcos C.;Lavandera, Iván;Gotor-Fernández, Vicente;De Gonzalo, Gonzalo;Gotor, Vicente [Tetrahedron,2011,vol. 67,# 16,p. 2858 - 2862] Location in patent:supporting information; experimental part
10318-17-9
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10318-16-8
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79-20-9
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56-75-7
799 suppliers
$19.69/20mg
10318-16-8
32 suppliers
$99.00/5mg
56-75-7
799 suppliers
$19.69/20mg
72-89-9
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10318-16-8
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![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
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56-75-7
799 suppliers
$19.69/20mg
10318-16-8
32 suppliers
$99.00/5mg