(S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide synthesis
- Product Name:(S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide
- CAS Number:918413-70-4
- Molecular formula:C12H27NO2SSi
- Molecular Weight:277.5
102191-92-4
343338-28-3
918413-70-4
(2-tert-butyldimethylsilylmethoxy)acetaldehyde (54.64 mL, 258.2 mmol) was dissolved in dichloromethane (DCM, 500 mL), (S)-2-methylpropane-2-sulfinamide (34.42 g, 284.0 mmol) was added followed by copper sulfate (103.0 g, 645.4 mmol). The reaction mixture was stirred at ambient temperature for 48 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and washed with DCM. The filtrate was concentrated and purified by silica gel column chromatography (eluent: 10-30% hexane solution of ethyl acetate) to afford (S,E)-N-(2-((tert-butyldimethylsilylmethoxy)ethylidene)-2-methylpropane-2-sulfenamide (67.3 g, 94% yield).
102191-92-4
151 suppliers
$10.00/250mg
343338-28-3
394 suppliers
$4.00/1g
918413-70-4
24 suppliers
inquiry
Yield:918413-70-4 94%
Reaction Conditions:
with copper sulfate in dichloromethane at 20; for 48 h;
Steps:
84.1
A mixture of 2-(tert-butyldimethylsilyloxy)acetaldehyde (54.64 mL,258.2 mmol) in DCM (500 mL) was treated with (S)-2-methylpropane-2-sulfinamide (34.42 g, 284.0 mmol), followed by copper sulfate (103.0 g, 645.4 mmol) at ambient temperature. After stirring for 48 hours, the mixture was filtered through Celite and washed with DCM. The mixture was concentrated and purified on silica gel (10-30% EtOAc in hexane) to provide (S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide (67.3 g, 94% yield).
References:
ARRAY BIOPHARMA INC.;ANDREWS, Steven W.;CONDROSKI, Kevin Ronald;DE MEESE, Lisa A.;FELL, Jay Bradford;FISCHER, John P.;LE HUEROU, Yvan;JOSEY, John A.;KOCH, Kevin;MIKNIS, Gregory F.;RODRIGUEZ, Martha E.;TOPALOV, George T.;WALLACE, Eli M.;XU, Rui WO2011/29027, 2011, A1 Location in patent:Page/Page column 121
18162-48-6
677 suppliers
$9.00/5g
918413-70-4
24 suppliers
inquiry
132835-15-5
5 suppliers
inquiry
918413-70-4
24 suppliers
inquiry