Sodium Iodide → (2R,3R)-3-[(2Z)-7-(Ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 4-Iodobutyl Carbonate

HRID 422891Notes

Reaction equation

HRID 422891 reaction equation
[C:1](=[O:38])([O:8][CH:9]1[CH2:13][CH:12]([OH:14])[C@H:11]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([NH:23][CH2:24][CH3:25])=[O:22])[C@H:10]1/[CH:26]=[CH:27]/[C@@H:28]([OH:37])[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[O:2][CH2:3][CH2:4][CH2:5][CH2:6]Cl.[I-:39].[Na+]>CC(C)=O>[C:1](=[O:38])([O:2][CH2:3][CH2:4][CH2:5][CH2:6][I:39])[O:8][CH:9]1[CH2:13][CH:12]([OH:14])[C@H:11]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([NH:23][CH2:24][CH3:25])=[O:22])[C@H:10]1/[CH:26]=[CH:27]/[C@@H:28]([OH:37])[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 866526684-Chlorobutyl (2R,3R)-3-[(2Z)-7-(Ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl Carbonate

Product 1

HCID 66675819(2R,3R)-3-[(2Z)-7-(Ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 4-Iodobutyl CarbonateYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chlorobutyl (2R,3R)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl carbonate (g-1; 25 mg, 0.045 mmol) was dissolved in acetone (0.9 mL). Sodium iodide (68 mg, 0.45 mmol) was added to the solution. The mix was microwaved at 135° C. for 35 mins and then concentrated under reduced pressure. The residue was dissolved in EA+water. EA phase was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated to give 23 mg (80%) crude iodide g-2, which was used immediately without further purification.

Workup

  1. customThe mix was microwaved at 135° C. for 35 mins
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EA+water
  4. customEA phase was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bbff0a89effc4790a2d766df453786ce
Source dataset
uspto-grants-2012_01
Patent number
US08101658B2

Reaction notes

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