Aluminium lithium hydride → HCID 89875978, compound

HRID 1487046Notes

Reaction equation

HRID 1487046 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:10]([C:13]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:18][C:14]=1[C:15](O)=[O:16])(=[O:12])=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:10]([C:13]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[CH:18][C:14]=1[CH2:15][OH:16])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 72189887HCID 72189887, compound

Product 1

HCID 89875978HCID 89875978, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-5-((tetrahydro-2H-pyran-4-yl)methoxy)benzoic acid (40 mg, 0.084 mmol) in tetrahydrofuran (THF) (1 mL) at 0° C. was added lithium aluminium hydride (1.0M in diethyl ether) (0.084 mL, 0.084 mmol) and the reaction mixture was stirred at 0° C. for 30 minutes then warmed to 25° C. for 1 hour. The reaction mixture was quenched carefully with water. The organic solvent was removed in vacuo and the remaining aqueous layer was extracted with ethyl acetate (20 mL×3). The organics were combined and concentrated in vacuo to give a yellow oil. The crude was then purified by mass directed autoprep (ammonium carbonate modifier). The appropriate fractions were concentrated under a stream of nitrogen in a Radleys blowdown apparatus to give the required product, 25.2 mg. LCMS [LCMS2] Rt 1.40 min, m/z (ES+) 462 (M+H).

Workup

  1. temperaturethen warmed to 25° C. for 1 hour
  2. customThe reaction mixture was quenched carefully with water
  3. customThe organic solvent was removed in vacuo
  4. extractionthe remaining aqueous layer was extracted with ethyl acetate (20 mL×3)
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customThe crude was then purified by mass
  8. concentrationThe appropriate fractions were concentrated under a stream of nitrogen in a Radleys blowdown apparatus

Sources & evidence

ORD record
ord-6483288a102e451eaf538de466df2d08
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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