Triethylamine → (-)-2-[2-(4-Chlorophenyl)benzyl]sulphinylacetamide
Reaction equation
C([C@](C([O-])=O)(O)[C@](CC)(O)C([O-])=[O:6])C.C(N)(=S)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=2[CH2:28][S:29][CH2:30][C:31]([NH2:33])=[O:32])=[CH:22][CH:21]=1.C(N(CC)CC)C.[O-]O.C1(C(C)C)C=CC=CC=1>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C.O.O>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:37]=[CH:36][CH:35]=[CH:34][C:27]=2[CH2:28][S:29]([CH2:30][C:31]([NH2:33])=[O:32])=[O:6])=[CH:24][CH:25]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
A solution of (S,S)-(−)-diethyl-tartrate (2.47 g; 0.012 mol; 0.4 eq.) in a solvent (3.5 vol. vs thioacetamide) was introduced in a reactor with an impeller, containing 6.5 vol (vs thioacetamide) of the same solvent. The solution was stirred and heated to 50° C. before adding 0.2 equivalent of titanium (IV) tetraisopropoxide (1.71 g; 1.77 mL; 0.006 mol; 0.2 eq) and water (QSP to achieve 0.095 eq. in the mixture) and kept stirring at 50° C. for one hour. In these conditions, the resulting chiral titanium complex had the stoichiometry of DET/Ti(OiPr)4/H2O: 2/1/0.475 and corresponded to 0.2 eq. with respect to the thioacetamide. After stirring at 50° C. for one hour, 1.0 eq. (8.75 g; 0.03 mol) of 2-[2-(4-chlorophenyl)benzyl]sulphanyl acetamide was added and contacted for 30 min. After cooling to 20° C., were successively added 0.2 eq. (0.61 g; 0.84 mL; 0.006 mol) of triethylamine and around 10 minutes later, 1.0 eq (4.57 g; 5.0 mL; 0.03 mol) of cumene hydroperoxide within less than 5 minutes.
Workup
- stirringkept stirring at 50° C. for one hour
- stirringAfter stirring at 50° C. for one hour
- temperatureAfter cooling to 20° C.
Sources & evidence
- ORD record
- ord-fdd8357e7e154c589dd13c6c3502a60a
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893111B2
Reaction notes
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