1,3-Propanedithiol → HCID 131718394, compound

Participants

Reaction Steps

2.04 ml of 1,3-propanedithiol were added dropwise to a stirred solution of 3.65 g of benzyl 2(R or S)-[[(RS)-(ethoxy)[1-(RS)-azido-5-tert.butoxycarbonylaminopentyl]phosphinyl]methyl]-4-methylvalerate and 2.83 ml of triethylamine in 80 ml of methanol. The mixture was stirred at room temperature overnight, the solvent was removed by evaporation and the residue was purified by flash chromatography on silica gel using 4% methanol/dichloromethane for the elution to give 3.25 g of benzyl 2(R or S)-[[(RS)-(ethoxy)[1-(RS)-amino-5-tert.butoxy carbonylaminopentyl]phosphinyl]methyl]-4-methylvalerate as an off-white foam; nmr (CDCl3): 7.36 (s,5H); 5.2-5.08 (m,2H); 4.6 (brs,1H); 4.2-3.98 (m,2H); 3.17-3.08 (m,2H); 3.0-2.76 (m,2H); 2.4-2.13 (m,1H): 2.0-1.25 (m,25H); 0.98-0.86 (m,6H); MS: 513 (M+H)+.

Provenance & Evidence