Stearoyl chloride → Octadecanoic acid 2-(2-aminoethoxy)ethyl ester hydrochloride

HRID 1251637Notes

Reaction equation

HRID 1251637 reaction equation
[C:1]([Cl:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl.[NH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][OH:28]>CN(C=O)C.CC(C)=O>[ClH:20].[NH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 8212Stearoyl chlorideHCID 18764647HO-Peg-amine hcl

Product 1

HCID 85772808Octadecanoic acid 2-(2-aminoethoxy)ethyl ester hydrochlorideYield 40%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Stearoyl chloride (6.4 g; 21 mmol) (commercial product) was added dropwise in 5 min to a solution of 2-(2-aminoethoxy)ethanol hydrochloride (2.9 g; 20 mmol) in DMF (50 mL) at room temperature to afford a suspension. After 16 h, the suspension was diluted with acetone and the precipitated solid filtered and washed with acetone. The crude was crystallized from EtOAc; the solid was filtered, washed with EtOAc and dried under reduced pressure to give the desired compound (3.3 g; 8 mmol). Yield 40%. Acidic titer (0.1 N NaOH): 93%. K.F.: 1.06%. The 1H-NMR, 13C-NMR, MS and IR spectra were consistent with the structure.

Workup

  1. customto afford a suspension
  2. filtrationthe precipitated solid filtered
  3. washwashed with acetone
  4. customThe crude was crystallized from EtOAc
  5. filtrationthe solid was filtered
  6. washwashed with EtOAc
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-67b5e58b80d44d878432b2777f542f9a
Source dataset
uspto-grants-2002_01
Patent number
US06342598B1

Reaction notes

Loading…