Methanesulfonyl chloride → HCID 86721883, compound

HRID 1049033Notes

Reaction equation

HRID 1049033 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([CH2:6][N:7]([CH2:35][CH:36]([CH3:38])[CH3:37])[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[O:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:50][S:51](Cl)(=[O:53])=[O:52].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:35][CH:36]([CH3:38])[CH3:37])[S:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C@@H:18]3[CH2:23][CH2:22][N:21]([S:51]([CH3:50])(=[O:53])=[O:52])[CH2:20][C@H:19]3[O:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:30])[CH3:31])[CH:26]([CH3:28])[CH3:27])=[CH:15][CH:16]=2)(=[O:9])=[O:10])=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86721882HCID 86721882, compound

Product 1

HCID 86721883HCID 86721883, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(4-chloro-benzyl)-N-isobutyl-4-((+/−)trans-3-triisopropylsilanyloxy-piperidin-4-yloxy)-benzenesulfonamide (185 mg, 304 μmol) in DCM (5 mL) was added DIPEA (106 μL, 609 μmol) followed by methanesulfonyl chloride (1 mL of a 231 μL, 3 mmol solution in 10 mL of DCM) and the reaction stirred at room temperature for 1 hour. Saturated aqueous NaHCO3 was then added, extracted with DCM, filtered through a phase separator and concentrated to give N-(4-Chloro-benzyl)-N-isobutyl-4-((+/−)trans-1-methanesulfonyl-3-triisopropylsilanyloxy-piperidin-4-yloxy)-benzenesulfonamide (271 mg, 100%). LCMS (m/z, Method A) ES+ 709 [M+23]+.

Workup

  1. extractionextracted with DCM
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-188ae97b186245b69684685f54371da6
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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