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Triethylamine → N6-(1-Oxooctadecyl)-L-lysine

HRID 1704291
Notes
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Reaction equation

HRID 1704291 reaction equation
Cl.[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[C:12](ON1C(=O)CCC1=O)(=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(N(CC)CC)C>O.CC(C)=O>[C:12]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]([C:9]([OH:11])=[O:10])[NH2:2])(=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69568L-Lysine monohydrochlorideHCID 3552761N-Succinimidyl Stearate

Product 1

HCID 104260N6-(1-Oxooctadecyl)-L-lysineYield 94.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962
Water
Solvent

Procedure

The title compound was prepared similarly as shown in example 3 from L-lysine monohydrochloride (0.94 g, 5.1 mmol) and succinimidyl stearate (1.94 g, 5.1 mmol) in the presence of triethylamine (2.15 ml, 15.3 mmol) in 9.4 ml of water and 9.4 ml of acetone. The product was washed with cold water and ethanol and then dried yielding 1.98 g (92.7%) of the title compound. Infrared: 1580-1590 cm-1 (ionized carboxyl group), 1635 and 1520-1535 cm-1 (amide bands).

Workup

  1. customThe title compound was prepared similarly
  2. washThe product was washed with cold water and ethanol
  3. customdried

Sources & evidence

ORD record
ord-93a32417b9ce4facac792140768c2194
Source dataset
uspto-grants-1978_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04126628

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes