S3I-201 synthesis
- Product Name:S3I-201
- CAS Number:501919-59-1
- Molecular formula:C16H15NO7S
- Molecular Weight:365.36
![Acetyl chloride, 2-[[(4-methylphenyl)sulfonyl]oxy]-](/CAS/20200611/GIF/54150-49-1.gif)
54150-49-1
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501919-59-1
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Yield: 63%
Reaction Conditions:
Stage #1:4-Aminosalicylic acid with sodium hydroxide in water at 20; for 0.166667 h;
Stage #2:2-chloro-2-oxoethyl 4-methylbenzenesulfonate with sodium carbonate in tetrahydrofuran;water at 0 - 20; for 2 h;
Steps:
11
A mixture of /7-amino salicylic acid (102 mg, 0.67 mmol) and NaOH (27mg, 0.67 mmol) in water (6 ml) was stirred at room temperature for 10 min until all of the solid material had dissolved. Na2COs (59 mg, 0.5561 mmol) was then added and the mixture cooled to 0 0C. A solution of 2-chloro-2-oxoethyl-4-methylbenzenesulfonate (4, 200 mg, 0.8044 mmol) in THF (2 ml) was injected rapidly and the resulting solution allowed to warm to room temperature and stirred for 2 h. Then reaction mixture was poured into a separating funnel containing diethyl ether. The phases were separated and the aqueous phase washed with a further portion of diethyl ether. The aqueous phase was acidified to pH 1 by addition of IN HCl solution and the product extracted into ethyl acetate. The ethyl acetate was washed twice with IN HCl solution and the organic phase was dried (Na2SO4), filtered and the solvent removed in vacuo. The resulting pale yellow solid was triturated with chloroform leaving 1 as a white powder (155 mg, 63%). 6H (400 MHz, DMSO) 2.37 (3H1 s, Me)5 4.68 (2H5 s, CH2), 6.93 (IH, d, J=7.4 Hz, ArH), 7.17 (IH, s, ArH), 7.46 (2H5 d, J=6.8 Hz, ArH), 7.69 (IH5 d, J=7.4 Hz, ArH), 7.81 (2H5 d, J=6.8 Hz, ArH), 10.32 (IH5 s, NH); δc (100.6 MHz5 DMSO) 21.8, 68.0, 107.0, 1 10.7, 128.5, 130.9, 131.7, 132.7, 144.5, 146.0, 162.8, 164.5, 172.2; MS (ES+) 366.0 (100%, [M+H]+), 388.0 (50%, [M+Na]+); (ion not detected in ES").
References:
H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE;UNIVERSITY OF SOUTH FLORIDA;UNIVERSITY OF CENTRAL FLORIDA WO2007/136858, 2007, A2 Location in patent:Page/Page column 63
39794-75-7
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39794-77-9
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98-59-9
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501919-59-1
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