Dimethylformamide dimethyl acetal → HCID 21905833, compound

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Reaction Steps

N,N-Dimethylformamide dimethyl acetal (16 ml, 121 mmol) was combined with 1-benzhydryl-3-benzylaminoazetidine-3-carboxylic acid amide (I-3A-50b; 3.03 g, 8.16 mmol) and heated to reflux. After 4 hours, the suspension was cooled and extracted from saturated aqueous NaHCO3 with ethyl acetate. The combined extracts were dried (Na2SO4) and concentrated, in vacuo, to give a crude solid (3.50 g). Purification of the residue on a Biotage™ Flash 40M column using 0-3% methanol in methylene chloride as eluant afforded I-3A-50c as a yellowish solid (1.92 g, 62%): +ESI MS (M+1) 382.3; 1H NMR (400 MHz, CD3OD) δ 8.66 (s, 1H), 7.59 (d, J=7.1 Hz, 2H), 7.49-7.11 (m, 13H), 5.12 (s, 2H), 4.44 (s, 1H), 3.31 (d, J=9.6 Hz, 2H), 3.20 (d, J=9.6 Hz, 2H).

Provenance & Evidence