Hydrochloric Acid → N-(2,4-dimethylphenyl)-3-(hydroxymethyl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 1487076Notes

Reaction equation

HRID 1487076 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:31][CH:32]([CH3:34])[CH3:33])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:23][CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[C:17]([CH:22]=1)[C:18](OC)=[O:19])(=[O:12])=[O:11].C([BH-](CC)CC)C.[Li+].Cl>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:31][CH:32]([CH3:34])[CH3:33])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:23][CH2:24][CH:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)=[C:17]([CH2:18][OH:19])[CH:22]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23664628LithiumtriethylborohydrideHCID 72189586methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-((tetrahydro-2H-pyran-4-yl)methoxy)benzoate

Product 1

HCID 72188991N-(2,4-dimethylphenyl)-3-(hydroxymethyl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-((tetrahydro-2H-pyran-4-yl)methoxy)benzoate (20 mg, 0.041 mmol) in tetrahydrofuran (THF) at 25° C. was added lithium triethylborohydride in THF (Superhydride®, 1.1 M, 0.037 mL, 0.041 mmol) and the reaction mixture stirring at 25° C. for 15 hours. Dilute HCl was added to reaction mixture and stirred for 10 minutes. The reaction mixture was then neutralised with base and the product was extracted into ethyl acetate (3×10 mL). The organics were combined and dried using a hydrophobic frit, then concentrated under a stream of nitrogen to give the crude product. This was purified by silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and concentrated under a stream of nitrogen to give the required product, 16.2 mg, as a colourless oil. LCMS [LCMS2] Rt 1.33 min, m/z (ES+) 462 (M+H).

Workup

  1. stirringstirred for 10 minutes
  2. extractionthe product was extracted into ethyl acetate (3×10 mL)
  3. customdried
  4. concentrationconcentrated under a stream of nitrogen
  5. customto give the crude product
  6. customThis was purified by silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient)
  7. concentrationconcentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-ed0d798d9d3243a8a700c42728387a84
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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