Dimethylformamide → HCID 86753218, compound

Participants

Reaction Steps

A solution of (4R)-1-(tert-butyloxycarbonyl)-4-amino-L-proline tert-butyl ester (134 mg, 0.468 mmol) and N,N'-bis(tert-butyloxycarbonyl)-S-methyl-isothiourea (150 mg, 0.515 mmol) in N,N-dimethylformamide (2 mL) was heated for 15 hours at 55° C. and 2 days at room temperature under a nitrogen atmosphere. The reaction mixture was diluted with diethyl ether, washed with water, dried (Na2SO4), and evaporated. The title compound was obtained pure by flash silica gel chromatography eluting with 10% ethyl acetate/hexane; yield 60.2 mg (24%). Mass spectrum: m/z 529 (M+1); 400 MHz 1H NMR (CD3OD): δ1.44-1.52 (4s, 36H); 2.08 (m, 1H); 2.59 (m, 1H); 3.42 (m, 1H); 3.78 (m, 1H); 4.23 (dd, 1H); 4.57 (m, 1H).

Provenance & Evidence