Sodium Chloride → HCID 86660406, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the chlorotitaniumtriisopropoxide (6.57 g, 25.2 mmol) in 80 mL dry THF at 0° C. was slowly added phenyllithium (2.0M solution in dibutylether, 12.6 mL, 25.2 mmol) and the mixture was stirred at 0° C. for 30 min, followed by a slow addition of a solution of (R)-2-Methyl-propane-2-sulfinic acid [(S)-1-(2-fluoro-5-nitro-phenyl)-1-methyl-3-oxo-propyl]-amide (4.2 g, 12.6 mmol) in 30 mL dry THF. The resulting reaction mixture was let to warm up to 23° C. and stirred at 23° C. for 2 h. The reaction medium was slowly poured into a stirred mixture of a saturated NaCl aqueous solution and ethylacetate, which was stirred for 15 min until precipitation occured. The suspension was filtered over celite, the filtrate was poured in a reparatory and extracted with water. The collected organic phase was dried over Na2SO4 and removal of solvent in vaccum yielded a crude yellow oil. The crude was purified by chromatography on silica using a mixture of heptane and ethylacetate which gave the desired diastereoisomer (R)-2-Methyl-propane-2-sulfinic acid [(1S,3S)-1-(2-fluoro-5-nitro-phenyl)-3-hydroxy-1-methyl-3-phenyl-propyl]-amide (1 g, 2.43 mmol, yield: 19.3%). MS (ISP): m/z=409.3 [(M+H)+] and a second diastereoisomer (R)-2-Methyl-propane-2-sulfinic acid [(1S,3R)-1-(2-fluoro-5-nitro-phenyl)-3-hydroxy-1-methyl-3-phenyl-propyl]-amide (2.6 g, 6.32 mmol, yield: 50.2%). MS (ISP):m/z=409.0 [(M+H)−].

Provenance & Evidence