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

HRID 480540

Reaction equation

HRID 480540 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 NaCH): 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-dd7104a734f3465185cca07e169ffb5a
Source dataset
uspto-grants-2003_11
Patent number
US06652834B2

Linked notes

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