Phenacyl bromide → HCID 86665860, compound

HRID 1619576Notes

Reaction equation

HRID 1619576 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:17]([O:19][C@@H:20]2[CH:25]3[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]3)[CH2:21]2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:36][CH2:37][C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:39]>CCOC(C)=O>[Br-:36].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:17]([O:19][C@@H:20]2[CH:25]3[CH2:24][CH2:23][N+:22]([CH2:37][C:38](=[O:39])[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)([CH2:27][CH2:26]3)[CH2:21]2)=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67606929HCID 67606929, compound

Product 1

HCID 86665860HCID 86665860, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)—((R)-quinuclidin-3-yl) 3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate (590 mg, 1.23 mmol) in EtOAc (15 ml), was added portionwise 2-bromo-1-phenylethanone (232 mg, 1.17 mmol). The reaction was stirred at RT for 16 hours. The solvent was evaporated, and the residue was triturated with Et2O, filtered and dried under vacuum to obtain (R)-3-((S)-3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoyloxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (720 mg, 86% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e500cfdcb8ac49868cce23af9ae52b36
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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