4-Bromophenacyl bromide → HCID 58209525, compound

HRID 1751644Notes

Reaction equation

HRID 1751644 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[C:12]([O:16][C:17]([N:19]1[CH2:23][C@@H:22]([CH3:24])[CH2:21][C@H:20]1[C:25]([OH:27])=[O:26])=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>CC#N.CCOC(C)=O>[CH3:24][C@@H:22]1[CH2:23][N:19]([C:17]([O:16][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:18])[C@H:20]([C:25]([O:27][CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=2)=[O:4])=[O:26])[CH2:21]1

Participants

6

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 8471TriethylamineHCID 26596883(4S)-1-(tert-Butoxycarbonyl)-4-methyl-L-proline

Product 1

HCID 58209525HCID 58209525, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-1-(4-bromophenyl)ethanone (505 mg, 1.82 mmol) in MeCN (18 mL) was added (2S,4S)-1-(tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid (500 mg, 2.18 mmol) and triethyl amine (0.27 mL, 2.0 mmol). After stirring for 15 h, the solution was diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (10% to 35% EtOAc/hexanes) to afford (2S,4S)-2-(2-(4-bromophenyl)-2-oxoethyl) 1-tert-butyl 4-methylpyrrolidine-1,2-dicarboxylate (748 mg, 97%).

Workup

  1. washwashed successively with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by silica column chromatography (10% to 35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-80bc0511158d4474bc2ad92ad24e8802
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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