Aluminium lithium hydride → HCID 57750951, compound

HRID 2283299Notes

Reaction equation

HRID 2283299 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=2[Cl:28])(=[O:20])=[O:19])=[C:13]([S:29](=[O:32])(=[O:31])[NH2:30])[CH:12]=1)C>C1COCC1>[Cl:28][C:22]1[C:23]([Cl:27])=[CH:24][CH:25]=[CH:26][C:21]=1[S:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][OH:9])=[CH:12][C:13]=1[S:29]([NH2:30])(=[O:32])=[O:31])(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68782330HCID 68782330, compound

Product 1

HCID 57750951HCID 57750951, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1M in THF, 6.6 mL, 6.6 mmol) was added slowly to a stirred solution of 4-(2,3-dichloro-benzenesulfonylamino)-3-sulfamoyl-benzoic acid ethyl ester (600 mg, 1.32 mmol) in dry THF (15 mL) at −10° C. The reaction mixture was allowed to warm to RT and stirring was continued for 4 h. The reaction mixture was then cooled to 0° C. and quenched by addition of water, followed by 1N HCl. The product was extracted with ethyl acetate, the combined organic phases were washed with water and brine, and dried over sodium sulfate. Volatiles were removed under reduced pressure and the crude product was purified by preparative HPLC to afford the title compound (60 mg, 11%).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customquenched by addition of water
  3. extractionThe product was extracted with ethyl acetate
  4. washthe combined organic phases were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customVolatiles were removed under reduced pressure
  7. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-89dd50a5b79a4f2ca4e0293ad8160c96
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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