Water → HCID 89435495, compound

HRID 1774686Notes

Reaction equation

HRID 1774686 reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H-].[Na+].[N+](C1C=CC([O:25][C:26](=O)[O:27][CH2:28][N:29]2[C:38]3[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][N:44]4[CH2:49][CH2:48][N:47]([C:50]5[C:58]6[CH:57]=[CH:56][S:55][C:54]=6[CH:53]=[CH:52][CH:51]=5)[CH2:46][CH2:45]4)[CH:37]=3)[CH:32]=[CH:31][C:30]2=[O:59])=CC=1)([O-])=O.O>C1COCC1>[CH2:1]([O:13][C:26](=[O:25])[O:27][CH2:28][N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][N:44]3[CH2:49][CH2:48][N:47]([C:50]4[C:58]5[CH:57]=[CH:56][S:55][C:54]=5[CH:53]=[CH:52][CH:51]=4)[CH2:46][CH2:45]3)[CH:37]=2)[CH:32]=[CH:31][C:30]1=[O:59])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 81931-DodecanolHCID 24758Sodium hydrideHCID 117855853HCID 117855853, compound

Product 1

HCID 89435495HCID 89435495, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Dodecanol (0.10 g) was dissolved in anhydrous THF (5 ml) under a nitrogen atmosphere and sodium hydride (about 55% oil) (25 mg) was added under ice-cooling with stirring. The reaction mixture was stirred at room temperature for 30 min under a nitrogen atmosphere, and then the mixture was ice-cooled. To the mixture was added a solution (5 ml) of carbonic acid 7-[4-(4-benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-2-oxo-2H-quinolin-1-ylmethyl ester 4-nitrophenyl ester obtained in Example 133 (0.33 g) in anhydrous THF using a cannula. Under a nitrogen atmosphere, the reaction mixture was stirred with ice-cooling for 2 hr, and at room temperature for 1 hr. Water was added to the reaction mixture to discontinue the reaction, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated by filtration. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (0.14 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 30 min under a nitrogen atmosphere
  3. temperaturecooled
  4. stirringUnder a nitrogen atmosphere, the reaction mixture was stirred with ice-
  5. temperaturecooling for 2 hr
  6. customthe reaction
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated by filtration
  10. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-dd04e76cdc8a43ac9dc977e1c66dbb7d
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

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