Sodium Iodide → HCID 58680103, compound

HRID 7398Notes

Reaction equation

HRID 7398 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C@H:13]([C:16]([NH2:18])=[O:17])[CH2:14][CH3:15])[C:9](=[O:19])[CH2:8]1)(=O)=O.[I-:20].[Na+]>C1COCC1>[I:20][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C@@H:13]([CH2:14][CH3:15])[C:16]([NH2:18])=[O:17])[C:9](=[O:19])[CH2:8]1

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 58680099HCID 58680099, compound

Product 1

HCID 58680103HCID 58680103, compoundYield 65,636,364%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 150 ml three necked flask fitted with magnetic stirrer and reflux condenser, under inert atmosphere, 6.88 g (23.5 nmoles) of {1-[(1S)-1-(aminocarbonyl)propyl]-6-oxo-3-piperidinyl}methyl methanesulfonate 24 were dissolved in 86 ml of THF. 3.9 g (25.9 mmoles, 1.1 eq) of sodium iodide were added in one portion and the mixture was brought to reflux. After 5 hours, 780 mg (5.2 mmoles, 0.22 eq) of sodium iodide were added and reflux continued for a total of 10 hours. After cooling down to 0° C., the mixture was filtered, the precipitate washed with THF, the combined organic fractions concentrated to dryness and purified by PrepLC (800 g SiO2, CH2Cl2/MeOH, 95/5) to give 7.21 g of crude compound. It was crystallised from 80 ml ethanol to give 5 g of pure iodide 13, 66% yield.

Workup

  1. temperaturereflux condenser
  2. temperatureto reflux
  3. temperaturereflux
  4. customcontinued for a total of 10 hours
  5. filtrationthe mixture was filtered
  6. washthe precipitate washed with THF
  7. concentrationthe combined organic fractions concentrated to dryness
  8. custompurified by PrepLC (800 g SiO2, CH2Cl2/MeOH, 95/5)
  9. customto give 7.21 g of crude compound
  10. customIt was crystallised from 80 ml ethanol

Sources & evidence

ORD record
ord-c7f6d570e3cd42f6a92e57cb911288ae
Source dataset
uspto-grants-2006_08
Patent number
US07087596B2

Reaction notes

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