Diisopropylethylamine → HCID 89462486, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-benzyl-3-cyano-1H-pyrrole-2-carboxylic acid (7.3 g, 32.4 mmol) in N,N-Dimethylformamide (DMF) (100 mL) was treated with sarcosine methyl ester hydrochloride (12 g, 86 mmol) and DIPEA (30 mL, 172 mmol), followed by HATU (26 g, 68.4 mmol). The mixture was stirred at 40° C. for 1 hour. The mixture was cooled to room temperature, brine was added and the resultant was extracted with ethyl acetate. The combined extracts were washed with HCl (1M), followed by brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford methyl 2-(1-benzyl-3-cyano-N-methyl-1H-pyrrole-2-carboxamido)acetate (9.2 g, 29.6 mmol, 91% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.31-7.38 (m, 3H). 7.20-7.26 (m, 2H) 6.73-6.78 (m, 1H) 6.40-6.46 (m, 1H) 5.17-5.26 (s, 2H) 4.16-4.26 (s, 2H) 3.71-3.80 (s, 3H) 3.06-3.15 (s, 3H); LCMS (m/z) ES+=312 (M+1).

Provenance & Evidence