Triethylamine → HCID 54463764, compound

HRID 1704290Notes

Reaction equation

HRID 1704290 reaction equation
Cl.[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[O:12](N1C(=O)CCC1=O)[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]CCCC)=O.C(N(CC)CC)C>O.CC(C)=O>[C:13]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]([C:9]([OH:11])=[O:10])[NH2:2])(=[O:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69568L-Lysine monohydrochlorideHCID 12535336Decanoic acid, 2,5-dioxo-1-pyrrolidinyl ester

Product 1

HCID 54463764HCID 54463764, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Similarly, as in example 2, the title compound was prepared using L-lysine monohydrochloride (7.30 g, 40 mmol) and succinimidyl caprate (10.7 g, 40 mmol) in the presence of triethylamine (16.8 ml, 120 mmol) in 35 ml of water and 36 ml of acetone. The product was washed with cold water and with cold ethanol then dried giving 9.04 g (78%) of the desired compound. Infrared: 1580-1590 cm-1 (ionized carboxyl), 1520-1540 and 1640 cm-1 (amide bands).

Workup

  1. customSimilarly, as in example 2, the title compound was prepared
  2. washThe product was washed with cold water and with cold ethanol
  3. customthen dried

Sources & evidence

ORD record
ord-adfdb3503ea942118de777214613dea8
Source dataset
uspto-grants-1978_11
Patent number
US04126628

Reaction notes

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