Ethyl Acetate → HCID 178521045, compound

Participants

Reaction Steps

A solution of 336 mg (0.5 mmol) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid (2-cyano-ethyl)-cyclopropyl-amide, 267 mg (5 mmol) NH4Cl and 325 mg (5 mmol) NaN3 in 10 ml DMF were heated at 70° C. for 22 h. 267 mg (5 mmol) NH4Cl and 325 mg (5 mmol) NaN3 together with 40 ml DMF were added and heated at 100° C. (24h) and at 120° C. (24h). The reaction was poured in H2O (0° C.)/EtOAc (3×). The organic phases were washed with aqueous 10% KHSO4, 10% NaCl solution and dried over Na2SO4. Purification by flash-chromatography on silicagel (CH2Cl2/MeOH: 99:1) gave 143 mg (40%) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid cyclopropyl-[2-(1H -tetrazol-5-yl)-ethyl]-amide, MS: 715 (MH+).

Provenance & Evidence