Water → HCID 86721882, compound

HRID 1049032Notes

Reaction equation

HRID 1049032 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C@@H:18]3[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]3[OH:24])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:38]([Si:41](OS(C(F)(F)F)(=O)=O)([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])([CH3:40])[CH3:39].O>C(Cl)Cl>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C@@H:18]3[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]3[O:24][Si:41]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:38]([CH3:40])[CH3:39])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 2724529Triisopropylsilyl trifluoromethanesulfonate2×HCID 86721881HCID 86721881, compound

Product 1

HCID 86721882HCID 86721882, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-chloro-benzyl)-4-((+/−)trans-3-hydroxy-piperidin-4-yloxy)-N-isobutyl-benzenesulfonamide (202 mg, 447 μmol) in DCM (10 mL) was added triethylamine (187 μL, 1.34 mmol) followed by triisopropylsilyltrifluoromethanesulfonate (132 μL, 492 μmol) and the reaction was stirred at room temperature for 1 hour. To the reaction was added Et3N (187 μL, 1.34 mmol) followed by triisopropylsilyltrifluoromethanesulfonate (132 μL, 492 μmol) and reaction stirred for a further 30 minutes at room temperature. Water was added, and the mixture was extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-10% MeOH in DCM) to give N-(4-chloro-benzyl)-N-isobutyl-4-((+/−)trans-3-triisopropylsilanyloxy-piperidin-4-yloxy)-benzenesulfonamide (189 mg, 70%). LCMS (m/z, Method A) ES+ 609 [M+1]+.

Workup

  1. stirringstirred for a further 30 minutes at room temperature
  2. extractionthe mixture was extracted with DCM
  3. filtrationfiltered through a phase separator
  4. concentrationconcentrated
  5. customthen purified by silica gel column chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-5f3515417b6b4492a25453c299b7b873
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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