Phenacyl bromide → HCID 86665848, compound

HRID 1619547Notes

Reaction equation

HRID 1619547 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:15]([O:17][C@@H:18]2[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]2)=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[Br:32][CH2:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:35]>C(Cl)Cl>[Br-:32].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][CH:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:15]([O:17][C@@H:18]2[CH:23]3[CH2:22][CH2:21][N+:20]([CH2:33][C:34](=[O:35])[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)([CH2:25][CH2:24]3)[CH2:19]2)=[O:16])(=[O:12])=[O:11])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67607656HCID 67607656, compound

Product 1

HCID 86665848HCID 86665848, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-quinuclidin-3-yl 2-(4-methoxyphenylsulfonamido)-2-phenylacetate hydrochloride (C68) (96 mg, 0.22 mmol) was dissolved in DCM and washed with 1M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated. The resulting solid was dissolved in EtOAc (2 ml) and 2-bromo-1-phenylethanone (49.2 mg, 0.25 mmol) was added. The reaction was stirred at RT for 3 hours, and then it was washed with aq. K2CO3, dried over Na2SO4, filtered and evaporated to obtain (3R)-3-(2-(4-methoxyphenylsulfonamido)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (75 mg; 53% yield).

Workup

  1. washwashed with 1M K2CO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe resulting solid was dissolved in EtOAc (2 ml)
  6. washit was washed with aq. K2CO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-6a585da42eac4cceb45cbf7ad968e6e4
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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