Hydrochloric Acid → Gsk-2981278

HRID 1487089Notes

Reaction equation

HRID 1487089 reaction equation
[Li+].[B-](CC)(CC)CC.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:39][CH:40]([CH3:42])[CH3:41])[S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:31][CH2:32][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:25]([CH:30]=2)[C:26](OC)=[O:27])(=[O:20])=[O:19])=[CH:13][CH:12]=1)[CH3:10].[Cl-].[NH4+].Cl>O1CCCC1>[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:39][CH:40]([CH3:41])[CH3:42])[S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:31][CH2:32][CH:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[C:25]([CH2:26][OH:27])[CH:30]=2)(=[O:19])=[O:20])=[CH:13][CH:12]=1)[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 23712863Lithium triethylborohydrideHCID 89875911HCID 89875911, compound

Product 1

HCID 89875987Gsk-2981278Yield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Super-Hydride® (1 M in tetrahydrofuran, 0.449 mL, 0.449 mmol) was added over 5 minutes, to a solution of methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-((tetrahydro-2H-pyran-4-yl)methoxy)benzoate (100 mg, 0.204 mmol) in tetrahydrofuran (THF) (2 mL) under nitrogen. The solution was stirred for 1 hour then was added to a 1:1 mixture of ammonium chloride solution and HCl (2 N, 10 mL). The mixture was extracted with tert-butyl methyl ether (TBME) (2×5 mL), then organics dried and evaporated. The residue was purified by silica (Si) chromatography (0-50% ethyl acetate-cyclohexane) to give the title compound as a white foam (75 mg). LCMS [LCMS1] Rt 1.28 min, m/z (ES+) 462 (M+H).

Workup

  1. extractionThe mixture was extracted with tert-butyl methyl ether (TBME) (2×5 mL)
  2. customorganics dried
  3. customevaporated
  4. customThe residue was purified by silica (Si) chromatography (0-50% ethyl acetate-cyclohexane)

Sources & evidence

ORD record
ord-badafb207efb4945b99776235ba544ba
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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