HCID 86585233, compound → HCID 9835681, compound

Participants

Reaction Steps

5-(6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoic acid (2b) is prepared from 6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (2a) (Basu, B., et al., Synth. Commun., 11, 10, 1981, 803-810) in an analogous manner to that described for 1b in example 1. 6.6 g (24.3 mmol) 1b are dissolved in 140 mL of CH2Cl2. To this solution is added sequentially 3.3 mL triethylamine, 6.9 g bis-(2-oxo-3-oxazolidinyl)-phosphorylchlorid, 3.0 g O-benzylhydroxylamine and another 10.2 mL triethylamine. After stirring over night the solution is washed with 2N HCl, then sat. NaCl sol., and evaporated. On treating with diethylether, 8.5 g 5-(6-Methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoic acid benzyloxy-amide (2c) is obtained as bright crystalls. Hydrogenation of 0.5 g of 2c in Methanol with Pd/BaCO3/Pb as a catalyst yields, after evaporation and treating with diethylether, 0.3 g of the title compound, MP 118-120° C.

Provenance & Evidence