1-Hydroxybenzotriazole → HCID 86618164, compound

Participants

Reaction Steps

A sample of tert-butyl ((1S,2S,5R)-2-amino-5-methoxycyclohexyl)methylcarbamate (2.53 g, 9.79 mmol) was dissolved in CH2Cl2 (50 ml) at room temperature. The solution was charged sequentially with 1-hydroxybenzotriazole (1.456 g, 10.77 mmol), N-carbobenzyloxy-L-methionine (4.16 g, 14.69 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.440 g, 12.73 mmol). The reaction mixture was stirred overnight. It was diluted with EtOAc and washed with saturated Na2CO3, followed by brine. The solution was dried (MgSO4), filtered, and concentrated in vacuo to yield tert-butyl ((1S,2S,5R)-2-((S)-2-benzyloxycarbonylamino-4-(methylthio)butanamido)-5-methoxycyclohexyl)methylcarbamate as a colorless sticky solid. LC/MS found [M+H]+=524.31.

Provenance & Evidence