Sodium Iodide → HCID 58680103, compound

HRID 1452511Notes

Reaction equation

HRID 1452511 reaction equation
CS(OC[CH:7]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]([C@H:14]([C:17]([NH2:19])=[O:18])[CH2:15][CH3:16])[CH2:8]1)(=O)=O.[I-:20].[Na+].[CH2:22]1COCC1>>[I:20][CH2:22][CH:12]1[CH2:7][CH2:8][N:9]([C@@H:14]([CH2:15][CH3:16])[C:17]([NH2:19])=[O:18])[C:10](=[O:13])[CH2:11]1

Participants

4

Reactant 3

HCID 5238Sodium Iodide2×HCID 8028TetrahydrofuranHCID 58680100HCID 58680100, compound

Product 1

HCID 58680103HCID 58680103, compoundYield 66%

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 mmoles) 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-f473030827d7423fb7c3b3f2109c7da1
Source dataset
uspto-grants-2009_01
Patent number
US07473697B2

Reaction notes

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