Sodium Hydroxide → HCID 56835965, compound

HRID 591202Notes

Reaction equation

HRID 591202 reaction equation
[CH2:1]([C:8]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([O:24][CH2:25][CH2:26][NH:27][S:28]([C:31]3[N:32]=[CH:33][N:34]([CH3:36])[CH:35]=3)(=[O:30])=[O:29])[CH:18]=2)[CH2:11][N:10]([C:12](OCC)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH2:1]([C:8]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH:18]=2)[O:24][CH2:25][CH2:26][NH:27][S:28]([C:31]2[N:32]=[CH:33][N:34]([CH3:36])[CH:35]=2)(=[O:29])=[O:30])[CH2:11][N:10]([CH3:12])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66747574HCID 66747574, compound

Product 1

HCID 56835965HCID 56835965, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To ethyl 3-benzyl-3-(4-fluoro-3-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)phenyl)azetidine-1-carboxylate (20.8 mg, 0.040 mmol) in tetrahydrofuran (1 ml) was added a 1M lithium aluminium hydride solution in tetrahydrofuran (0.121 ml, 0.121 mmol) and refluxed for 2 h. Cooled down to room temperature and 2N NaOH was slowly added and extracted twice with dichloromethane, washed with sodium bicarbonate and brine, dried over MgSO4, filtered, evaporated and purified by flash silica gel chromatography on 4 g SiO2-cartridge using 10% MeOH in dichloromethane affording 8.9 mg of the titled compound as a white solid.

Workup

  1. temperaturerefluxed for 2 h
  2. extractionextracted twice with dichloromethane
  3. washwashed with sodium bicarbonate and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by flash silica gel chromatography on 4 g SiO2-cartridge

Sources & evidence

ORD record
ord-65f25b73afb64ecbbf4ae1b966457f62
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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