Water → HCID 86721884, compound

HRID 1049034Notes

Reaction equation

HRID 1049034 reaction equation
[Cl:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][N:7]([CH2:39][CH:40]([CH3:42])[CH3:41])[S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C@@H:18]3[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20][C@H:19]3[O:28][Si](C(C)C)(C(C)C)C(C)C)=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:39][CH:40]([CH3:41])[CH3:42])[S:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C@@H:18]3[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:25])=[O:26])[CH2:20][C@H:19]3[OH:28])=[CH:15][CH:16]=2)(=[O:9])=[O:10])=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86721883HCID 86721883, compound

Product 1

HCID 86721884HCID 86721884, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(4-Chloro-benzyl)-N-isobutyl-4-((+/−)trans-1-methanesulfonyl-3-triisopropylsilanyloxy-piperidin-4-yloxy)-benzenesulfonamide (271 mg) in THF (5 mL) was added a 1 M solution of tetrabutylammonium fluoride in THF (609 μL, 609 mmol) and the reaction was stirred at room temperature for 30 minutes. Water was added and then extracted with EtOAc, washed with brine, dried with Na2SO4 then concentrated, purified by silica gel column chromatography (0-75% EtOAc in cyclohexane) and freeze dried to give the title compound (107 mg). 1H NMR (400 MHz, DMSO): δ 7.76 (d, 2H), 7.36-7.37 (m, 4H), 7.20 (d, 2H), 5.54 (d, 1H), 4.41 (td, 1H), 4.23 (s, 2H), 3.70-3.72 (m, 1H), 3.52 (dd, 1H), 3.42 (d, 1H), 3.04-3.08 (m, 1H), 2.94 (s, 3H), 2.90 (dd, 1H), 2.83 (d, 2H), 2.12-2.19 (m, 1H), 1.57-1.59 (m, 2H), 0.67 (d, 6H). LCMS (m/z, Method B) ES+ 531 [M+1]+.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. concentrationthen concentrated
  5. custompurified by silica gel column chromatography (0-75% EtOAc in cyclohexane)
  6. customfreeze dried

Sources & evidence

ORD record
ord-a37e1e8b6a7c4922bdb787c7e94bd11a
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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