benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate synthesis
- Product Name:benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate
- CAS Number:1194550-59-8
- Molecular formula:C17H20ClNO4S
- Molecular Weight:369.86
![L-Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester](/CAS/20180703/GIF/1289646-78-1.gif)
1289646-78-1
1194550-59-8
The general procedure for the synthesis of benzyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride from benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate is as follows: firstly, using sodium bicarbonate (3 eq.) and tert-butyl dicarbonate (Boc2O, 1.1 eq.) in a solvent mixture of dioxane and water. tert-butoxycarbonyl (Boc) protection of the amino group of bromophenylalanine, and the reaction afforded compound 7 in 98% yield.Subsequently, the reaction was carried out by cuprous iodide (0.4 eq.), cesium carbonate (0.5 eq.), L-proline (0.8 eq.), and the sodium salt of methanesulfinic acid (3.9 eq.) in dimethylsulfoxide (DMSO) for 9 hr. at 95-100 °C, during which two Additional addition of cuprous iodide (0.2 eq.) and L-proline (0.4 eq.) introduced the methanesulfonyl functional group, which was isolated in 96% yield to give compound 8. Next, using benzyl alcohol (1.1 eq.), 4-dimethylaminopyridine (DMAP, 0.1 eq.) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC, 1.0 eq. ), the carboxylic acid group of compound 8 was converted to a benzyl ester to give compound 9 in 99% yield. Finally, the deprotection reaction of the amino group was carried out by adding a dioxane solution of 4N HCl to a dichloromethane solution of compound 9 at 0 °C to isolate the hydrochloride salt of the free amino group, compound 10, in 94% yield.
1289646-78-1
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1194550-59-8
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Yield:1194550-59-8 94%
Reaction Conditions:
with hydrogenchloride in 1,4-dioxane;dichloromethane at 0;
Steps:
2; 2A; 2B Example 2
[00121] t-Butylcarbamate (Boc) protection of the amino group of bromophenylalaninewas accomplished, using sodium bicarbonate (3 equivalents), t-butyl dicarbonate (Boc2O, 1.1equivalent) in dioxane and water, to obtain compound 7 in 98% yield. A methyl sulfone functionality was introduced by treating the bromo compound 7 with copper iodide (0.4 equivalents), cesium carbonate (0.5 equivalents), L-proline (0.8 equivalents), and the sodium salt of methanesulfinic acid (3.9 equivalents) in dimethylsulfoxide (DMSO) at 95-100°C for a totalof 9 hours, with two further additions of copper iodide (0.2 equivalents) and L-proline (0.4 equivalents) during that period. Compound 8 was isolated in 96% yield. The carboxylic acid of compound 8 was converted to the benzyl ester, compound 9, in 99% yield, using benzyl alcohol (1 .1 equivalent), dimethylaminopyridine (DMAP, 0.1 equivalent) and N-(3 - dimethylaminopropyl)-N-ethylcarbodiimide (EDC, 1.0 equivalent). The amino group ofcompound 9 is deprotected by adding a 4N solution of HC1 in dioxane to compound 9 at 0°C in methylene chloride. The HC1 salt of the free amino species, compound 10 was isolated in 94% yield.
References:
SARCODE BIOSCIENCE INC.;ZELLER, James, Robert;VENKATRAMAN, Sripathy;BROT, Elisabeth, C.A.;IYER, Subashree;HALL, Michael WO2014/18748, 2014, A1 Location in patent:Paragraph 00120; 00121; 00122; 00123; 00124; 001
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1194550-59-8
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1289646-76-9
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1194550-59-8
142 suppliers
$43.00/1g