Acetone → HCID 86753774, compound

HRID 1417545Notes

Reaction equation

HRID 1417545 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:28](OS(C)(=O)=O)[CH2:27][CH2:26][C@@:9]32[O:13][CH2:12][C@H:11]([C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=2[O:22][CH:23]([CH3:25])[CH3:24])[CH2:10]3)=[CH:4][CH:3]=1.[I-:34].[Na+].[CH3:36]C(C)=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[C@@H:28]([CH2:36][I:34])[CH2:27][CH2:26][C@@:9]32[O:13][CH2:12][C@H:11]([C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=2[O:22][CH:23]([CH3:25])[CH3:24])[CH2:10]3)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 86753772HCID 86753772, compound

Product 1

HCID 86753774HCID 86753774, compound

Procedure

The methanesulfonate from Step B was dissolved in acetone (2 mL). Sodium iodide (25 mg, 0.167 mmol) was added, and the mixture was heated at reflux temperature until TLC indicated disappearance of starting material. The cooled reaction mixture was evaporated, the residue taken up in methylene chloride, washed with water, 10% sodium thiosulfate solution, saturated brine solution, dried (Na2SO4), and evaporated. The title compound was obtained pure by silica gel chromatography eluting with 15% diethyl ether/hexane; yield 35 mg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature until TLC
  3. customThe cooled reaction mixture
  4. customwas evaporated
  5. washwashed with water, 10% sodium thiosulfate solution, saturated brine solution
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-8c6d0200fb304ab1b00dc6bfb645883c
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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