Potassium Iodide → (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-{2-[3-methoxy-4-(3-phenyl-2-propyn-1-yloxy)-phenyl]-ethyl}-amide

HRID 1018652Notes

Reaction equation

HRID 1018652 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:21])[C@@H:12]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1[O:22][CH3:23].[C:24]1([C:30]#[C:31][CH2:32]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C[O-].[Na+].[I-].[K+].[Cl-].[Na+]>CO>[CH3:23][O:22][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:21])[C@@H:12]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:7][C:2]=1[O:1][CH2:32][C:31]#[C:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 105173333-Phenylprop-2-yn-1-yl 4-methylbenzene-1-sulfonateHCID 10882483(S)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-methanesulfonylamino-3-methyl-butyramideHCID 10942334Sodium Methoxide

Product 1

HCID 11070536(S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-{2-[3-methoxy-4-(3-phenyl-2-propyn-1-yloxy)-phenyl]-ethyl}-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g of (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-amide and 2.7 g of toluene-4-sulfonic acid (3-phenyl-2-propyn-1-yl) ester are heated at reflux for 3 hours together with 12 ml of 1M sodium methanolate solution with the addition of 20 mg of potassium iodide in 50 ml of methanol. The reaction mixture is cooled and introduced into 200 ml of saturated sodium chloride solution. Extraction is carried out twice using 200 ml of ethyl acetate each time. The organic phases are combined, dried over magnesium sulfate and concentrated. The residue is subjected to flash chromatography on silica gel with ethyl acetate/n-hexane (2:1), yielding (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-{2-[3-methoxy-4-(3-phenyl-2-propyn-1-yloxy)-phenyl]-ethyl}-amide, which is recrystallised from ethyl acetate/n-hexane, m.p. 130-132° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionExtraction
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-36f5ff5ed51e4236bf20fe10bed81d9a
Source dataset
uspto-grants-2002_11
Patent number
US06482859B1

Reaction notes

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