Acetyl bromide → HCID 86660312, compound

HRID 453702Notes

Reaction equation

HRID 453702 reaction equation
[C:1]([Br:4])(=[O:3])[CH3:2].[Br-].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:40])[CH2:14][N+:15]23[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]2)[C@@H:17]([O:23][C:24](=[O:39])[C@@H:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:16]3)=[CH:9][CH:8]=1.C(Cl)Cl.CO.CC#N.O>C(Cl)Cl>[Br-:4].[C:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:40])[CH2:14][N+:15]23[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22]2)[C@@H:17]([O:23][C:24](=[O:39])[C@@H:25]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:16]3)=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 10482Acetyl bromideHCID 18373917Acetonitrile--water (1/1)HCID 21226129Dichloromethane methanolHCID 86660310HCID 86660310, compound

Product 1

HCID 86660312HCID 86660312, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl bromide (10 μl, 0.14 mmol) was added 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 TEA (19.5 μl, 0.14 mmol) and DCM (3 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the crude product was purified first by trituration with Et2O, then by flash-chromatography (DCM/MeOH=95/5) and finally by preparative HPLC (eluents: CH3CN/H2O) to obtain (R)-1-(2-(4-acetoxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (24 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-2f0840fb0adc4e4e9f9bfb2e9fb84581
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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