1-Hydroxybenzotriazole → HCID 86757665, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of pentafluorophenyl (2R,3S)-2-(3-phenyl-1-propyl)-3-(formyl-2-tetrahydropyranyloxyamino)hexanoate (90 mg, 0.166 mmol) in DMF (0.5 mL) is added (2S)-6-benzyloxycarbonylamino-2-aminohexanoic acid 1,3,4-thiadiazol-2-ylamide (78 mg, 0.215 mmol) and HOBt ( 2.2 mg, 0.017 mmol). The resulting solution is heated to 50° C. and is stirred for 18 h. The reaction mixture is cooled to 25° C., concentrated in vacuo, diluted with 20 mL of EtOAc, and washed with 1 M aqueous sodium carbonate solution. The organic layer is dried over magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (elution with 2:1 EtOAc-hexane) to provide (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(3-phenyl-1-propyl)hexanoic acid [(1S)-5-benzyloxycarbonylamino-1-(1,3,4-thiadiazol-2-ylcarbamoyl)-1-pentyl]amide as an oil (24.1 mg, 25% yield). APCI-MS m/z 745 (M+Na)+.

Provenance & Evidence