Phenacyl bromide → HCID 86643224, compound

HRID 1255069Notes

Reaction equation

HRID 1255069 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][CH:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]([O:14][C@@H:15]2[CH:20]3[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]3)[CH2:16]2)=[O:13])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].Br[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32]>C(OCC)(=O)C>[CH:12]([O-:14])=[O:13].[C:1]([C:4]1[CH:5]=[C:6]([NH:10][CH:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]([O:14][C@@H:15]2[CH:20]3[CH2:19][CH2:18][N+:17]([CH2:30][C:31](=[O:32])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([CH2:22][CH2:21]3)[CH2:16]2)=[O:13])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 59401159HCID 59401159, compound

Product 1

HCID 86643224HCID 86643224, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-Quinuclidin-3-yl 2-(3-acetylphenylamino)-2-phenylacetate (C53) (134 mg, 0.35 mmol) and 2-bromo-1-phenylethanone (85.0 mg, 0.42 mmol) are dissolved in ethyl acetate (5 mL) and stirred at RT for 2 hours. EtOAc is evaporated and the resulting crude oil is first purified by flash chromatography (DCM/MeOH=95/5) and then by preparative HPLC. The fractions containing the product are combined and concentrated under vacuum to remove the organic solvent. The resulting aqueous solution is freeze-dried obtaining the title compound as a white-foam (77.7 mg, 40% yield, formate salt, mixture of diastereoisomers).

Workup

  1. customEtOAc is evaporated
  2. customthe resulting crude oil is first purified by flash chromatography (DCM/MeOH=95/5)
  3. additionThe fractions containing the product
  4. concentrationconcentrated under vacuum
  5. customto remove the organic solvent
  6. customThe resulting aqueous solution is freeze-dried

Sources & evidence

ORD record
ord-ed3d92a36bf84697919bb9f15f803766
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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