4-Methylmorpholine → HCID 69783948, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 315 mg (1.80 mmol) of N-methoxycarbonyl-(L)-valine (Example 73b) are activated with 795 mg (1.80 mmol) of BOP and 267 mg (1.80 mmol) of HOBT in 12 ml of a 0.3M solution of NMM in DMF and, after 15 min, reacted for 48 h with 240 mg (0.60 mmol) of 1-[2(R)-hydroxy-3(R)-amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-hydrazine (in the form of the hydrochloride salt) (can be prepared analogously to 1-[2(S)-hydroxy-3(S)-amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-hydrazine hydrochloride salt (Example 10a, =H-[PheNNCha]-H.3HCl) from (D)-N-Boc-phenylalanine). The reaction mixture is concentrated by evaporation under HV and the residue is partitioned between 3 portions of methylene chloride, 2 portions of saturated NaHCO3 solution and brine. Column chromatography (SiO2, methylene chloride/methanol 19:1) and digestion with methylene chloride/DIPE yields the pure title compound: TLC Rf (B')=0.60; tRet (V)=14.7 min; FAB-MS (M+H)+ =606.

Provenance & Evidence