Chlorine → HCID 131731398, compound

Temperature

7 °C

Chlorine was bubbled trough a solution of L(+)-lysine monohydrochloride (150 g, 821 mmol) in HCl (36%) at 70° C. The mixture was irradiated with a medium pressure mercury lamp while stirring. After 2 h the reaction mixture was cooled to 7° C. and a seed crystal was added to induce crystallization. After one hour the resulting crystals were filtered off and the crude product was triturated twice with MeOH. The crystals were collected to afford 4.1 as a white solid. Yield: 12.6 g, 49.7 mmol, 6%. 1H-NMR (300 MHz, DMSO-d6) δ 8.81 (br s, αNH3, 3H), 8.43 (br s, εNH3, 3H), 4.48 (m, γCH, 1H), 3.96 (br s, αCH, 1H), 2.94 (m, εCH2, 2H), 2.31 (m, βCH2+δCH, total 3H), 2.04 (m, δCH, 1H). 13C-NMR (75 MHz, DMSO-d6) δ 169.9 (C═O), 56.6 (γCH), 49.6 (αCH), 38.4 (εCH2), 36.1 (βCH2), 35.1 (δCH2). LC-MS program 3: Rt=1.05 min, MS ES+ (amu): 180.94 [M+H]+.

1. customThe mixture was irradiated with a medium pressure mercury lamp
2. additiona seed crystal was added
3. customcrystallization
4. filtrationAfter one hour the resulting crystals were filtered off
5. customthe crude product was triturated twice with MeOH
6. customThe crystals were collected

ORD record

ord-3bd4620ec1fc4e86ab6bff6adc2a682e

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729009B2