HCID 15896334, compound → HCID 9934470, compound

HRID 479461Notes

Reaction equation

HRID 479461 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][OH:41])[CH:35]=3)[CH2:29][CH2:28]2)[C:12]1=[O:42])(C(C)(C)C)(C)C>O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Cl-].[Na+].O>[OH:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:13]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][OH:41])[CH:35]=3)[CH2:29][CH2:28]2)[C:12]1=[O:42]

Participants

5

Reactant 1

HCID 15896334HCID 15896334, compound

Product 1

HCID 9934470HCID 9934470, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 11078149TBAF tetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the oil obtained by (a) in 2 ml of tetrahydrofuran (THF), 0.31 ml of 1N tetrabutylammonium fluoride/THF solution was added and stirred for 30 minutes at room temperature. Saturated brine was added thereto and the reaction mixture was extracted with ethyl acetate and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the obtained residue was purified by silica gel column chromatography (chloroform—5% methanol/chloroform) to give 63 mg (0.13 mmol) of the title compound as colorless oil.

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (chloroform—5% methanol/chloroform)

Sources & evidence

ORD record
ord-d91a557770a24bb88d69e11b69ce59c8
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

Loading…