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

HRID 1634859Notes

Reaction equation

HRID 1634859 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 a solution 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-b94860fa3c504ad783551749e3a961c6
Source dataset
uspto-grants-2003_01
Patent number
US06509032B1

Reaction notes

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