4-Toluenesulfonyl chloride → HCID 86761068, compound

Participants

Reaction Steps

To a solution of (S) isobutyl 2-hydroxybutyrate (2.72 Kg) and p-toluenesulfonylchloride (3.6 Kg) in ethyl acetate (14 L) at 20° C. was added a solution of DABCO (286 g) and triethylamine (4.7 L) in ethyl acetate (10 L) over 2 h. The reaction was aged at 20-25° C. for 4 h. The mixture was washed with three times with water (10 L, 2 L and 2 L) and the organics concentrated and solvent switched into toluene. The concentrated toluene solution of (S) 2-isobutyl tosylbutyrate was used as is in coupling reaction. Alternatively, acetonitrile can be used in place of ethyl acetate, in which case the reaction proceeds faster.

Provenance & Evidence