2-(Chloroacetyl)thiophene → HCID 86672928, compound

HRID 1910493Notes

Reaction equation

HRID 1910493 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[N:10]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[C@@H:12]([NH:18][C:19](=[O:36])[O:20][CH:21]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:11]2>C(OCC)(=O)C>[Cl-:1].[CH3:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:20][C:19]([NH:18][C@@H:12]2[CH:13]3[CH2:14][CH2:15][N+:10]([CH2:2][C:3](=[O:4])[C:5]4[S:6][CH:7]=[CH:8][CH:9]=4)([CH2:17][CH2:16]3)[CH2:11]2)=[O:36])=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 70673881HCID 70673881, compound

Product 1

HCID 86672928HCID 86672928, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-(thiophen-2-yl)ethanone (12.0 mg, 0.07 mmol) was added to a solution of (4-methoxyphenyl)(phenyl)methyl(R)-quinuclidin-3-ylcarbamate (22.0 mg, 0.06 mmol, prepared as in example 3) in ethyl acetate (2 ml). The reaction was stirred at room temperature for two days. The reaction was evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=95/5) to obtain (3R)-3-(((4-methoxyphenyl)(phenyl)methoxy)carbonylamino)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (23 mg, mixture of diastereoisomers).

Workup

  1. customThe reaction was evaporated to dryness
  2. customThe crude was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-3687e6c7d1684c47b3c5ee1fcefcfa57
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

Loading…