Aluminium lithium hydride → HCID 86588216, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2 mL THF and 0.8 mL 1M LiAlH4 solution in ether was cooled to −65° C. in a chloroform/dry ice bath. A mixture if 0.18 g (0.29 mmol) N-methoxy-N-methyl--3-[4-(3-methyl-thioureido)-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-succinamic acid tert-butyl ester in 3 mL THF was added dropwise and the reaction mixture was stirred 30 min at −65° C. TLC analysis showed starting material consumed. The reaction was quenched cold with 1 mL 1M aqueous potassium sodium tartrate solution and allowed to reach room temperature. The product was partioned between 75 mL brine and 50 mL EtOAc. The product was extracted with 50 EtOAc, the combined organic extracts dried over anhydrous magnesium sulfate, filtered, concentrated and purified on silica with 1:1 EtOAc:hexanes to give 0.84 g (52%) of 3-[4-(3-methyl-thioureido)-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester as a colorless glass. MS (APCI) m/z 573 (M+1).

Provenance & Evidence