Reaction #75004

ord-d12b3c586e7f4196ac0a0810b72b08cc

Reaction equation

[Na+].[OH-]
NaOH
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)CCC(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C
cholesteryl hydrogen succinate
CCCCN(CCCC)CCCC
tributylamine
CC(C)COC(=O)Cl
isobutyl chloroformate
→
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
cholesterol

Reactants

[Na+].[OH-]
NaOH
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)CCC(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C
cholesteryl hydrogen succinate
CCCCN(CCCC)CCCC
tributylamine
CC(C)COC(=O)Cl
isobutyl chloroformate

Reagents

None

Solvents

C1COCCO1
Dioxane
O
water
C1COCCO1
p-dioxane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe solution was cooled
  2. 2
    Othercold for 30 minutes
  3. 3
    workup.ADDITIONthe mixture was added in one portion to a stirred
  4. 4
    Temperaturecooling
  5. 5
    OtherThe material was then dialyzed against water

Procedure

20.25 Grams (41.8 mmoles) of cholesteryl hydrogen succinate (sold by Aldrich Chemicals) and 19.8 ml (83.4 mmoles) of tributylamine were dissolved in 540 ml of Dioxane. The solution was cooled and treated with 5.3 ml (5.7 g, 41.7 mmoles) of isobutyl chloroformate. The reaction was permitted to proceed in the cold for 30 minutes, and then the mixture was added in one portion to a stirred, cooled solution of 50.0 g (41.7 mmoles) of bovine serum albumin in 1100 ml of water, 750 ml of p-dioxane, and 50 ml of 1 N NaOH. Stirring and cooling was continued for 6 hours. The material was then dialyzed against water and lyophilized to yield a stable white powder useful as a cholesterol standard.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04175074uspto-grants-1979_11