Pyridine → HCID 86762401, compound
Reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].N1[CH:11]=[CH:10][CH:9]=CC=1.Cl[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14].NCCS.CCCCCC.[C:29]([O:32]CC)(=[O:31])C>ClCCl.C(Cl)(Cl)Cl.CO>[CH2:16]([O:15][C:13]([NH:2][CH2:3][CH2:4][S:5][C:29]([O:32][CH2:11][CH:10]=[CH2:9])=[O:31])=[O:14])[CH:17]=[CH2:18]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -10 °C
Procedure
Cysteamine hydrochloride (1 g, 8.8 mM) was dissolved in dichloromethane (DCM, 6 mL) containing pyridine (3 mL) and the solution cooled (−10° C.). A solution of allyl chloroformate (2 mL, 18.86 mM) in DCM (3 mL) was dropwise added into the stirred cold cysteamine solution. Following the addition, reaction temperature was allowed to rise to room temperature (22° C.), when tlc (Hexane-Ethyl acetate, 2:1; 6:1 v/v) indicated product. Methanol (2 mL) was added followed by CHCl3 (10 mL), stirring continued for 2 h following which the reaction mixture was transferred into a separating funnel and washed (general method). Organic layer was dried (MgSO4), filtered, evaporated under vacuum to a syrup and column chromatographed (prepacked silica, 40 g) using hexane-ethyl acetate (12:1 v/v) to give the name compound (1.6 g).
Workup
- additionthe addition, reaction temperature
- customto rise to room temperature
- customwas transferred into a separating funnel
- washwashed (general method)
- dry with materialOrganic layer was dried (MgSO4)
- filtrationfiltered
- customevaporated under vacuum to a syrup and column
- customchromatographed (prepacked silica, 40 g)
Sources & evidence
- ORD record
- ord-33654e92dc3e4a8480a8b1a050adb1bb
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08728453B2
Reaction notes
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