Water → HCID 86753811, compound

HRID 1417613Notes

Reaction equation

HRID 1417613 reaction equation
[Si]([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:35])[C@@H:23]([CH3:34])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:33])([CH3:32])[C@H:28]5[O:31][C@H:29]5[CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[O:31]1[C@H:29]2[CH2:30][C@:20]34[C@H:26]([C:27]([CH3:33])([CH3:32])[C@@H:28]12)[CH2:25][CH2:24][C@H:23]([CH3:34])[C@@:21]3([CH3:35])[CH2:22][C:10]1[C:9]([OH:8])=[CH:17][C:16]2[C:15](=[O:18])[NH:14][CH2:13][C:12]=2[C:11]=1[O:19]4

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86753810HCID 86753810, compound

Product 1

HCID 86753811HCID 86753811, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above Compound (43b) (28 mg, 0.056 mmol) in 2.0 ml of THF was added dropwise 75 μl (0.075 mmol) of 1M tetrabutylammonium fluoride under ice-cooling, and the mixture stirred for 2 hours at the same temperature. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed sequentially with 1N HCl, water, an aqueous saturated sodium hydrogen carbonate solution, and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=10:1) to give 16 mg (74%) of Compound (43a).

Workup

  1. temperaturecooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed sequentially with 1N HCl, water
  4. dry with materialan aqueous saturated sodium hydrogen carbonate solution, and water, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-9ba7a578cbc54774a1915ed6d705431b
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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