N-Phenylanthranilic Acid → (S)-1-[2-(Phenylamino)benzoyl]-2-pyrrolidinemethanol

Participants

Reaction Steps

2.13 g (10 mmol) of N-phenylanthranilic acid, 1.35 g (10 mmol) of 1-hydroxybenzotriazole hydrate, 1.0 ml (10 mmol) of L-prolinol and 2.06 g (10 mmol) of DCC in 50 ml 1:1/methylene chloride:DMF. The coupling was carried out as described in Example 25 for the coupling of the acid and S(+)-2-pyrrolidinemethanol. Clean product of the title compound was obtained in virtually quantitative yield as a brownish gum without chromatographic purification. TLC (90:10/CH2Cl2 :MeOH): Rf =0.75. 1H NMR (CDCl3) δ: 7.50(bs,1H); 6.75-7.36 (m,9H); 4.65-4.80(m,1H); 4.25-4.40 (m,1H); 3.38-3.85(m,4H); 1.55-2.15(m,4H).

Provenance & Evidence