Sodium Iodide → HCID 68977194, compound

HRID 2218566Notes

Reaction equation

HRID 2218566 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[NH:12][C:13](=[O:19])[CH2:14][CH:15]([CH3:18])[CH2:16]Cl)=[O:5])[CH3:2].[I-].[Na+].[H-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[N:12]1[CH2:16][CH:15]([CH3:18])[CH2:14][C:13]1=[O:19])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 68979449HCID 68979449, compound

Product 1

HCID 68977194HCID 68977194, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

cis-2-(4-Chloro-3-methyl-butyrylamino)-cyclohexanecarboxylic acid ethyl ester (895 mg) was dissolved in absolute DMF (20 ml) under argon at RT. Sodium iodide (463 mg) and sodium hydride (55%) (270 mg) were added; a white suspension was obtained. The mixture was then stirred for 2 hours at room temperature. The reaction mixture was poured into ice/water containing saturated NH4Cl solution and the aqueous layer was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 95/5/0.5) to give the product as a 1:1 mixture of epimers as a light yellow liquid (402 mg). MS (ESI): 254.1 (M+H+).

Workup

  1. customa white suspension was obtained
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 95/5/0.5)
  8. customto give the product

Sources & evidence

ORD record
ord-05869659dc404e18a31ed7ae9cc54bda
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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