Tetrabutylammonium Fluoride → HCID 71543441, compound

HRID 1746418Notes

Reaction equation

HRID 1746418 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:37][CH:38]([CH3:40])[CH3:39])[S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[C:31]([CH3:36])=[N:32][O:33][C:34]=3[CH3:35])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH3:36][C:31]1[C:30]([CH2:29][O:28][C:25]2[CH:24]=[CH:23][C:22]([S:19]([N:18]([C:15]3[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[CH:13][CH:14]=3)[CH2:37][CH:38]([CH3:40])[CH3:39])(=[O:21])=[O:20])=[CH:27][CH:26]=2)=[C:34]([CH3:35])[O:33][N:32]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86731593HCID 86731593, compound

Product 1

HCID 71543441HCID 71543441, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(4-(3-((tert-butyldimethylsilyl)oxy)propyl)phenyl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutylbenzenesulfonamide (276.8 mg, 0.472 mmol) was dissolved in Tetrahydrofuran (THF) (10 mL). To this solution was added TBAF in THF (1M) (0.707 mL, 0.707 mmol), and the solution was left to stir for 1 hr at room temperature. The reaction mixture was concentrated on the Biotage V10 evaporator, extracted to the organic phase of an aqueous workup between ethyl acetate (10 mL) and water (10 mL) followed by a brine (10 mL) wash. The organic phase was passed through a hydrophobic frit, and concentrated in vacuo, before being dissolved in DCM and loaded onto a silica column and purified by column chromatography on Biotage II Flashmaster (20 g silica (Si), 40 mins, 0-50% EtOAc in cyclohexane). The relevant fractions were combined and condensed and the sample was freeze dried using a minimum of dioxane in water, to give the final product, 67%. LCMS (M+1) 473.1, RT 1.16 mins.

Workup

  1. waitthe solution was left
  2. concentrationThe reaction mixture was concentrated on the Biotage V10 evaporator
  3. extractionextracted to the organic phase of an aqueous workup between ethyl acetate (10 mL) and water (10 mL)
  4. washwash
  5. concentrationconcentrated in vacuo
  6. dissolutionbefore being dissolved in DCM
  7. custompurified by column chromatography on Biotage II Flashmaster (20 g silica (Si), 40 mins, 0-50% EtOAc in cyclohexane)
  8. customcondensed
  9. customdried

Sources & evidence

ORD record
ord-5fa72941696b4e4985d97d8f5b9bad05
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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