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Tributylamine → Cholesterol

HRID 46726
Notes
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Reaction equation

HRID 46726 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:35])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:34])[CH2:22][CH2:23][C@H:24]([O:26]C(CCC(O)=O)=O)[CH2:25][C:20]4=[CH:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].C(N(CCCC)CCCC)CCC.ClC(OCC(C)C)=O.[OH-].[Na+]>O1CCOCC1.O>[CH3:8][CH:6]([CH2:5][CH2:4][CH2:3][C@H:2]([C@@H:9]1[C@:13]2([CH3:35])[C@H:12]([C@H:17]3[C@H:16]([CH2:15][CH2:14]2)[C@:21]2([CH3:34])[C:20]([CH2:25][C@H:24]([CH2:23][CH2:22]2)[OH:26])=[CH:19][CH2:18]3)[CH2:11][CH2:10]1)[CH3:1])[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7622TributylamineHCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 65082Cholesteryl hemisuccinate

Product 1

HCID 5997Cholesterol

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 312751,4-DioxaneSolvent2×

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.

Workup

  1. temperatureThe solution was cooled
  2. customcold for 30 minutes
  3. additionthe mixture was added in one portion to a stirred
  4. temperaturecooling
  5. customThe material was then dialyzed against water

Sources & evidence

ORD record
ord-d12b3c586e7f4196ac0a0810b72b08cc
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04175074

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes