4-Bromophenacyl bromide → HCID 58209590, compound

HRID 1751659Notes

Reaction equation

HRID 1751659 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[C@@H:23]([CH3:24])[CH2:22][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:23]1[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][CH2:22]1

Participants

6

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 8471TriethylamineHCID 15516206(5S)-1-(tert-Butoxycarbonyl)-5-methyl-L-proline

Product 1

HCID 58209590HCID 58209590, compoundYield 82.5%

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,5S)-1-(tert-butoxycarbonyl)-5-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 40% EtOAc/hexanes) to afford (2S,5S)-2-(2-(4-bromophenyl)-2-oxoethyl) 1-tert-butyl 5-methylpyrrolidine-1,2-dicarboxylate (640 mg, 82%).

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 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2a89e2b0724e4e2ab1b5149be3b70065
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

Loading…