Water → HCID 87505693, compound

HRID 2234786Notes

Reaction equation

HRID 2234786 reaction equation
[O:1]([CH:9]([CH3:49])[CH2:10][C:11]1[C:19]2[C:18]([Cl:20])=[N:17][CH:16]=[N:15][C:14]=2[N:13]([C@@H:21]2[O:36][C@H:35]([CH2:37][O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=3[Cl:47])[C@@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])[C@@:22]2([CH3:48])[OH:23])[CH:12]=1)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>C1COCC1>[Cl:20][C:18]1[C:19]2[C:11]([CH2:10][CH:9]([OH:1])[CH3:49])=[CH:12][N:13]([C@@H:21]3[O:36][C@H:35]([CH2:37][O:38][CH2:39][C:40]4[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=4[Cl:47])[C@@H:24]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=4[Cl:34])[C@@:22]3([CH3:48])[OH:23])[C:14]=2[N:15]=[CH:16][N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 87505912HCID 87505912, compound

Product 1

HCID 87505693HCID 87505693, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 4.2 (800 mg, 1.01 mmol) in THF (20 mL) was added a 1.0 M solution of tetrabutylammonium fluoride in THF (1.5 mmol) at room temperature. The colorless solution was stirred for 4 hr at room temperature and then diluted by addition of 150 mL of CH2Cl2 and water (50 mL). The aqueous layers were extracted three times with CH2Cl2, and then dried over Na2SO4, filtered and evaporated. Purification by silica gel column chromatography using 1-2% MeOH in CH2Cl2 as eluent gave the desired compound 4.3 (460 mg, 67%) as a white solid.

Workup

  1. extractionThe aqueous layers were extracted three times with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-5bd494fe835b4ad79b4fb4e018b569da
Source dataset
uspto-grants-2010_05
Patent number
US07713941B2

Reaction notes

Loading…