Diisopropylethylamine → 1-((S)-1-(4-bromophenyl)ethyl)-4-phenyl-1,3-diazepan-2-one

A stirred solution of N1—((1S)-1-(4-bromophenyl)ethyl)-4-phenylbutane-1,4-diamine dihydrochloride (19.5 mg, 0.046 mmol) and i-Pr2NEt (0.10 mL, 0.56 mmol) in CH2Cl2 (8 mL) was cooled in an ice bath and solid triphosgene (4.6 mg, 0.015 mmol) was added. The ice bath was allowed to melt and the mixture was stirred overnight at rt. The mixture was diluted with ether (90 mL), washed with 5% aq HCl (20 mL) and satd aq NaHCO3 (20 mL), and dried over MgSO4. Removal of the solvent left a residue (17.5 mg) which was purified by preparative HPLC to afford 1-((S)-1-(4-bromophenyl)ethyl)-4-phenyl-1,3-diazepan-2-one (1.4 mg, 8%). LC-MS (3 min) tR=2.05 min, m/z=375, 373.

1. washwashed with 5% aq HCl (20 mL)
2. dry with materialdried over MgSO4
3. customRemoval of the solvent
4. waitleft a residue (17.5 mg) which
5. customwas purified by preparative HPLC

ORD-Eintrag

ord-f2f7e3249dc045fbb590d86dd9fd973b

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08598160B2