Methanol → Methyl L-lysinate dihydrochloride

HRID 1472983Notes

Reaction equation

HRID 1472983 reaction equation
[ClH:1].[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[CH3:12]O>>[ClH:1].[ClH:1].[CH3:12][O:10][C:9](=[O:11])[C@H:3]([CH2:4][CH2:5][CH2:6][CH2:7][NH2:8])[NH2:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 69568L-Lysine monohydrochloride

Product 1

HCID 117778Methyl L-lysinate dihydrochlorideYield 91.6%

Procedure

To a mixture of L-Lysine-Hydrochloride (100 g) in 1.75 L of methanol at 0° C. was bubbled dry HCl for 7 hours. The crude solid product was filtered, dried to get pure L-Lysine methyl ester dihydrochloride (117 g, 91.6%) as a white powder with a melting point of 204.5-206° C. The compound was characterized by 1H NMR (DMSO-d6) δ 1.48 (m, 2H, CH2), 1.68 (m, 2H, CH2), 1.90 (m, 2H, CH2), 2.80 (m, 2H, CH2), 3.78 (s, 3H, Ester), 4.00 (t, 1H, CH), 8.20 (bs, 2H, NH2), 8.70 (bs, 2H, NH2).

Workup

  1. customwas bubbled dry HCl for 7 hours
  2. filtrationThe crude solid product was filtered
  3. customdried

Sources & evidence

ORD record
ord-5675f099b83540abbd1eb3e0955a6eb9
Source dataset
uspto-grants-2015_04
Patent number
US09012677B2

Reaction notes

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