Iodine → 3-(N-(N',N'-dimethylaminoethane)carbamoyl)cholesterol

HRID 429703Notes

Reaction equation

HRID 429703 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:31])[CH2:14][CH2:15][CH:16]3[C@@:21]4([CH3:30])[CH2:22][CH2:23][CH:24]([O:26][C:27](Cl)=[O:28])[CH2:25][C:20]4=[CH:19][CH2:18][CH:17]3[CH:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][NH2:36].II>C(Cl)(Cl)Cl>[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:31])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:30])[CH2:22][CH2:23][C@H:24]([O:26][C:27]([NH:36][CH2:35][CH2:34][N:33]([CH3:37])[CH3:32])=[O:28])[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]

Participants

5

Reactant 3

HCID 807IodineHCID 66053N,N-DimethylethylenediamineHCID 54236888C28H45ClO2

Product 1

HCID 1152343-(N-(N',N'-dimethylaminoethane)carbamoyl)cholesterol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Compound XIV was synthesized by mixing absolution of cholesteryl chloroformate (0.5 mmol) in chloroform with a solution of N,N-dimethylethylenediamine (9.1 mmol) in chloroform in a dry ice-ethanol bath. The solvent and the unreacted amine were removed in vacuo. Compound XIV was purified by two successive recrystallizations in ethanol. (Yield, 65%) TLC (chloroform:methanol=65:35) showed a single spot (Rf=0.37) when developed with iodine. The product was characterized by proton NMR.

Workup

  1. customThe solvent and the unreacted amine were removed in vacuo
  2. customCompound XIV was purified by two successive recrystallizations in ethanol
  3. custom(Yield, 65%) TLC (chloroform:methanol=65:35)

Sources & evidence

ORD record
ord-bd0f7d1f36db4ac781327365cb4c7f60
Source dataset
uspto-grants-2001_11
Patent number
US06319516B1

Reaction notes

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