Stearoyl chloride → Stearic Acid

HRID 580787Notes

Reaction equation

HRID 580787 reaction equation
[C:1](Cl)(=[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].[OH:21]N1C(=O)CCC1=O.C(N(CC)CC)C.C1(=O)NC(=O)CC1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].O>[C:1]([OH:19])(=[O:21])[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

8

Reactant 4

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 11439SuccinimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 5281Stearic Acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

0.5 g of stearoyl chloride was dissolved in 2 ml of 1,4-dioxane, and 0.29 g of N-hydroxysuccinimide and 0.1 ml of triethylamine were added, and the mixture was stirred at room temperature for 3 h. 1 ml of water was added to the mixture, and the pH was adjusted to 5 by addition of alkali. 60 μl of a succinimide-activated stearic acid solution were mixed with 2.5 ml of hirudin solution (21 mg/ml in 0.1 M sodium carbonate pH 9) and 2.5 ml of dioxane, and the mixture was incubated at room temperature with stirring for 12 h. The mixture was then purified by preparative RP-HPLC (see Example 2). The derivatives elute at 48% B, 54% B, 62% B and 74% B. The specific acitivities were 9,600 U/mg, 12,400 U/mg, 12,800 U/mg and 840 U/mg.

Workup

  1. additionthe pH was adjusted to 5 by addition of alkali
  2. customwas incubated at room temperature
  3. stirringwith stirring for 12 h
  4. customThe mixture was then purified by preparative RP-HPLC (see Example 2)
  5. washThe derivatives elute at 48% B, 54% B, 62% B and 74% B

Sources & evidence

ORD record
ord-441eb81188fd45e78f5af59f67bdfbe8
Source dataset
uspto-grants-1999_07
Patent number
US05919762

Reaction notes

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