2-Chloroacetophenone → HCID 86665862, compound

HRID 1619582Notes

Reaction equation

HRID 1619582 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:10]([NH:12][CH:13]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:14]([O:16][C@@H:17]1[CH:22]2[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]2)[CH2:18]1)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:37][CH2:38][C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40]>CCOC(C)=O.C(#N)C>[Cl-:37].[C:1]([O:5][C:6]([NH:8][CH:9]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:10]([NH:12][CH:13]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:14]([O:16][C@@H:17]1[CH:22]2[CH2:21][CH2:20][N+:19]([CH2:38][C:39](=[O:40])[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([CH2:24][CH2:23]2)[CH2:18]1)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 107572-Chloroacetophenone2×HCID 67605946HCID 67605946, compound

Product 1

HCID 86665862HCID 86665862, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(2-(tert-butoxycarbonylamino)-2-phenylacetamido)-2-phenylacetate (210 mg, 0.42 mmol) in EtOAc (3 ml) and acetonitrile (3 ml), was added 2-chloro-1-phenylethanone (65.8 mg, 0.42 mmol), and the reaction was stirred at RT for 15 hours. More 2-chloro-1-phenylethanone (19.7 mg, 0.13 mmol) was added, and the reaction was stirred at RT for 24 hours. The solvent was evaporated, and the crude was purified by flash chromatography (DCM/MeOH=94/6 to 93/7) to obtain (3R)-3-(2-(2-(tert-butoxycarbonylamino)-2-phenylacetamido)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (65.3 mg, 23.7% yield).

Workup

  1. stirringthe reaction was stirred at RT for 24 hours
  2. customThe solvent was evaporated
  3. customthe crude was purified by flash chromatography (DCM/MeOH=94/6 to 93/7)

Sources & evidence

ORD record
ord-4c103a4b62514e69829e86d407e3cedf
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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