(R)-N-((S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide(WXC04800) synthesis
- Product Name:(R)-N-((S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide(WXC04800)
- CAS Number:336105-31-8
- Molecular formula:C12H15BrF3NOS
- Molecular Weight:358.22
![2-Propanesulfinamide, N-[(4-bromophenyl)methylene]-2-methyl-, [N(Z),S(R)]-](/CAS/20211123/GIF/1448681-98-8.gif)
Yield:336105-31-8 76%
Reaction Conditions:
with tetrabutylammonium acetate in N,N-dimethyl-formamide at 0 - 5; for 1.5 h;
Steps:
2 N-[(1S)-1-(4-Bromophenyl)-2,2,2-trifluoro-ethyl]-(R)-2-methyl-propane-2-sulfinamide
Preparation 2
N-[(1S)-1-(4-Bromophenyl)-2,2,2-trifluoro-ethyl]-(R)-2-methyl-propane-2-sulfinamide
Add neat (trifluoromethyl)trimethylsilane (109 mL, 0.74 mol) at 0° C. to a stirred solution of tetrabutylammonium acetate (88 g, 0.29 mol) and (N-Z)-N-[(4-bromophenyl)methylene]-(R)-2-methyl-propane-2-sulfinamide (85 g, 0.29 mol) in DMF (1.2 L) at 0° C.
Stir the mixture at 0-5° C. for 90 minutes.
Add saturated aqueous ammonium chloride solution (1.2 L) and extract with EtOAc (4*400 mL).
Combine the organic extracts and sequentially wash with water then brine (2*1 L); dry over magnesium sulphate; filter; and concentrate the filtrate under reduced pressure.
Triturate the residue with hexane (200 mL) for 10 minutes; filter; and dry the filtrate under vacuum to afford the title compound as a yellow solid (81 g, 76% yield, >98 de). MS (m/z): 358 (M+1).
References:
US2013/197039,2013,A1 Location in patent:Paragraph 0039; 0040
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