1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid (1H-tetrazol-5-ylmethyl)-amide

Participants

Reaction Steps

A solution of 200 mg (0.34 mmol) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid and 42 mg (0.38 mmol) N-hydroxy-2-pyridone in 15 ml CH2Cl2 were treated at 0° C. with 72 mg (0.38 mmol) of EDCI. After 3.5h at RT, it was cooled (0° C.) and treated with 37 mg (0.38 mmol) of 5-aminomethyl-tetrazol. The reaction was stirred over night at RT, 2 ml DMF were added and after 4 h at RT the reaction was extracted with EtOAc/aqueous saturated NaHCO3. The organic phase was washed with aqueous 10% KHSO4, dried over Na2SO4 and purified by flash-chromatography on silicagel (CH2Cl2/MeOH 9:1) to give 100 mg (44%) of (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid (1H-tetrazol-5-ylmethyl)-amide, mp: 135-145 slow dec, MS: 661 (MH+).

Provenance & Evidence