Benzoyl chloride → 2,6-di-(N-benzoyl)amino-3-hydroxyheptanedioic acid, diethyl ester

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Reaction Steps

Amine (9) (4.0 g, 10.9 mM) is taken up in CH2Cl2 (150 ml), cooled in an ice bath, and treated with Et3N (1.67 ml, 12 mM). Benzoyl chloride (1.27 ml, 10.9 mM) is added slowly over a period of 5 minutes and stirring continued at 4° C. for 1 hour. The reaction is warmed to room temperature and stirred overnight. This mixture is washed with 5% aqueous HCl (3×100 ml), saturated aqueous NaCl (3×100 ml), dried over anhydrous MgSO4, filtered and evaporated to dryness in vacuo to yield a white foam. The latter is purified by flash chromatography on silica gel eluting with 12% acetone/CH2Cl2 to yield 3.0 g (59% yield) of the desired product as a white foam. 'H-N.M.R. (CDCl3 /TMS): δ=1.19 (t, 3H, --CH2CH3); 1.22 (t, 3H, --CH2CH3); 1.40-2.27 (m, 4H, --CH2CH2 --); 4.19 (2q, 4H, --CH2CH3); 4.00-5.00 (4H, 10H, 2>CHCO2Et, CHOH); 6.90-7.86 ppm (m, 12H, 2NH and 2Ph).

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