Methanesulfonyl chloride → HCID 86660311, compound

HRID 453701Notes

Reaction equation

HRID 453701 reaction equation
[Br-:1].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:36])[CH2:10][N+:11]23[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]2)[C@@H:13]([O:19][C:20](=[O:35])[C@@H:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12]3)=[CH:5][CH:4]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39].CC#N.O>C(Cl)Cl>[Br-:1].[CH3:37][S:38]([O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:36])[CH2:10][N+:11]23[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18]2)[C@@H:13]([O:19][C:20](=[O:35])[C@@H:21]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:12]3)=[CH:5][CH:4]=1)(=[O:40])=[O:39]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 18373917Acetonitrile--water (1/1)HCID 86660310HCID 86660310, compound

Product 1

HCID 86660311HCID 86660311, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (diastereomer 1 of I71) (70 mg, 0.13 mmol) in DCM, were sequentially added methanesulfonyl chloride (9.9 μl, 0.13 mmol) and then TEA (17.7 μl, 0.13 mmol). The reaction mixture was stirred at room temperature for two days. The solvent was evaporated, and the crude product was purified first by trituration with Et2O and then by preparative HPLC (eluents: CH3CN/H2O) to obtain (R)-1-(2-(4-(methylsulfonyloxy)phenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (25.5 mg, 31.9% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified first by trituration with Et2O

Sources & evidence

ORD record
ord-c91b61eac1d14d80bdc23b7548724906
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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