2-chloro-N-(1,2-oxazol-3-yl)acetamide → (3R)-1-(2-(isoxazol-3-ylamino)-2-oxoethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride

HRID 404624Notes

Reaction equation

HRID 404624 reaction equation
[C:1]1([CH:7]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:25][CH2:26][C:27]([NH:29][C:30]1[CH:34]=[CH:33][O:32][N:31]=1)=[O:28]>CCOC(C)=O.C(#N)C>[Cl-:25].[O:32]1[CH:33]=[CH:34][C:30]([NH:29][C:27](=[O:28])[CH2:26][N+:13]23[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]2)[C@@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:12]3)=[N:31]1

Participants

5

Reactant 2

HCID 133629182-chloro-N-(1,2-oxazol-3-yl)acetamideHCID 71603247(R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate

Product 1

HCID 86688885(3R)-1-(2-(isoxazol-3-ylamino)-2-oxoethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane chlorideYield 37.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (100 mg, 0.30 mmol) in EtOAc (2 ml) and acetonitrile (1 ml), was added 2-chloro-N-(isoxazol-3-yl)acetamide (58.7 mg, 0.36 mmol). The reaction was stirred at room temperature for 30 hours and then the solvents were evaporated. Purification by flash chromatography (DCM/MeOH=9/1) followed by trituration with Et2O afforded the title compound (55 mg, 36.9% yield) as an off-white solid.

Workup

  1. customthe solvents were evaporated
  2. customPurification by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-9d21ace8bebc47ce938dac6aa3c0460c
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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