Triethylamine → HCID 10449402, compound

Participants

Reaction Steps

To a mixture of 3.6 g of (R)-3-chloromandelic acid, 3.5 g of S(-)-2-amino-7-hydroxy-1,2,3,4-tetrahydronaphtalene monohydrate (PREPARATION III) and 7.7 g of BOP in 60 ml of anhydrous methylene chloride under nitrogen stream, there is added 2.7 ml of triethylamine. The solution obtained is stirred for 5 hours at room temperature, then 400 ml of ethyl acetate are added thereto and the organic phase is washed with water, separated and evaporated to dryness. The residue thus obtained is treated with 150 ml of N sodium hydroxide and extracted with ethyl ether. The organic phase is eliminated. The aqueous phase is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase thus obtained is washed with water, dried over sodium sulfate, filtered and evaporated to dryness. The oil thus obtained is purified by flash chromatography (elution with a 70/30 mixture of ethyl acetate/cyclohexane). An amount of 4 g (63%) of N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(R)-3-chloromandelamide is obtained as a very thick whittish oil that is treated with petroleum ether; a solid having an undefined melting point is obtained; [alpha]=-95° (methanol, c= 1%). This product is identical with the compound SR 58587 of Example 9(b), the (S, R) configuration of which is thus confirmed.

Provenance & Evidence