Sodium Iodide → Methyl 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-5-iodopentanoate

HRID 2084916Notes

Reaction equation

HRID 2084916 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH3:25])[CH:16]([CH2:21][CH2:22][CH2:23]Cl)[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[I-:26].[Na+]>CC(C)=O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH3:25])[CH:16]([CH2:21][CH2:22][CH2:23][I:26])[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 22644971Methyl 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-5-chloropentanoate

Product 1

HCID 22644817Methyl 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-5-iodopentanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4.80 g of methyl 2-[{[4-(2-butynyloxy)phenyl]-sulfonyl}(methyl)amino]-5-chloropentanoate of Step 1 and 15 g of sodium iodide in 25 ml of acetone was stirred at room temperature for 3 days. Solvent was removed under reduced pressure, and the residue was washed with water. The product was dried to give methyl 2-[{[4-(2-butynyloxy)phenyl]-sulfonyl}(methyl)amino]-5-iodopentanoate as a pale yellow solid, Electrospray Mass Spec 480.2 (M+H)+.

Workup

  1. customSolvent was removed under reduced pressure
  2. washthe residue was washed with water
  3. customThe product was dried

Sources & evidence

ORD record
ord-a22b6d61be0e40f3b9bf1ef4dac637db
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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