Water → HCID 59867815, compound

HRID 1662756Notes

Reaction equation

HRID 1662756 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:55][CH3:56])=[C:15]([C:17]2([N:44]3[CH2:53][C@H:52]([OH:54])[CH2:51][C@H:45]3[C:46]([N:48]([CH3:50])[CH3:49])=[O:47])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[N:19]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=3[O:38][C:39]([F:42])([F:41])[F:40])(=[O:29])=[O:28])[C:18]2=[O:43])[CH:16]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.O>C1COCC1>[Cl:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]([S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[O:38][C:39]([F:40])([F:42])[F:41])(=[O:28])=[O:29])[C:18](=[O:43])[C:17]2([N:44]1[CH2:53][C@H:52]([OH:54])[CH2:51][C@H:45]1[C:46]([N:48]([CH3:49])[CH3:50])=[O:47])[C:15]1[CH:16]=[C:11]([CH2:10][CH2:9][OH:8])[CH:12]=[CH:13][C:14]=1[O:55][CH3:56]

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 67429229HCID 67429229, compound

Product 1

HCID 59867815HCID 59867815, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500 mg of the compound obtained in Step 216-6 in THF (5.0 ml) was added dropwise a solution of 1 mol/L TBAF/THF (2.6 ml) under ice cooling. The solution was stirred at room temperature for two hours. Water was added to the reaction solution and the resulting mixture was extracted with EtOAc. The extract was dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: CHCl3/MeOH=8/1; v/v) to obtain 320 mg of the title compound (light yellow solid).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. dry with materialThe extract was dried over Na2SO4
  3. customthe drying agent was separated by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: CHCl3/MeOH=8/1; v/v)

Sources & evidence

ORD record
ord-b9894b04a19d4da0834e1ba190bd7803
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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