Diisopropylethylamine → HCID 86596943, compound

Participants

Reaction Steps

A solution of (1R,3R,4S)-3-butyl-N1-isopropyl-N1-methylcyclohexane-1,4-diamine (81 mg, 0.35 mmol; see Example 3a, Step 4) in 1:1 DMF/methylene chloride (5 mL) was charged successively with HATU (162 mg, 0.43 mmol), N-Boc D-Alanine (67 mg, 0.35 mmol), and N,N-diisopropylethylamine (0.31 mL, 1.77 mmol). The reaction was stirred for 16 h at RT, concentrated in vacuo, and diluted with EtOAc. The organic phase was washed successively with sat. NaHCO3, water, 1N HCl, water, and brine before being dried (sodium sulfate), filtered, and concentrated in vacuo to afford tert-butyl (R)-1-((1S,2R,4R)-2-butyl-4-(isopropyl(methyl)amino)cyclohexylamino)-1-oxopropan-2-ylcarbamate. MS found: (M+H)+=398.4.

Provenance & Evidence