Hydrochloric Acid → HCID 54196894, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of dimethyl methylphosphonate (19.5 ml) in anhydrous tetrahydrofuran (300 ml) is added a 1.72 M solution of n-butyl lithium in n-hexane (107 ml) at -50° C. Thirty minutes later, to the mixture is added in portions 2-(2-methoxy-4-formylphenoxymethylcarbonylamino)benzothiazole (20.5 g) under nitrogen atmosphere. The mixture is stirred at -50° C. for one hour, and thereto is added water. The mixture is acidified with conc. hydrochloric acid, and extracted with ethyl acetate. The extract is washed with water, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=200:1→30:1) to give dimethyl {2-[3-methoxy-4-(2-benzothiazolylaminocarbonylmethoxy)phenyl]-2-hydroxyethyl}phosphonate (19.0 g).

Provenance & Evidence