4-Bromophenacyl bromide → HCID 59611327, compound

HRID 1751594Notes

Reaction equation

HRID 1751594 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][CH:22]([CH2:24][O:25][CH3:26])[CH2:21][C@H:20]1[C:27]([OH:29])=[O:28])=[O:18])([CH3:15])([CH3:14])[CH3:13].CCN(CC)CC>CC#N.CCOC(C)=O>[CH3:26][O:25][CH2:24][CH:22]1[CH2:23][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:18])[C@H:20]([C:27]([O:29][CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=2)=[O:4])=[O:28])[CH2:21]1

Participants

6

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 8471TriethylamineHCID 69673149HCID 69673149, compound

Product 1

HCID 59611327HCID 59611327, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-1-(4-bromophenyl)ethanone (2.3 g, 8.39 mmol) and (S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid (2.61 g, 10.06 mmol) in MeCN (100 mL) was added Et3N (1.26 mL, 9.24 mmol). After stirring over night, the solution was diluted with EtOAc, washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography to yield product (3.32 g).

Workup

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-18bcd96524fa41b48c1d4fb99853523e
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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