4-Bromophenacyl bromide → HCID 59610929, compound

HRID 1751332Notes

Reaction equation

HRID 1751332 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]([OH:24])[CH2:21][C@H:20]1[C:25]([OH:27])=[O:26])=[O:18])([CH3:15])([CH3:14])[CH3:13].CCN(CC)CC>CC#N.CCOC(C)=O.C([O-])(O)=O.[Na+].[Cl-].[Na+].O>[OH:24][C@@H:22]1[CH2:23][N:19]([C:17]([O:16][C:12]([CH3:13])([CH3:14])[CH3:15])=[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

8

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 8471TriethylamineHCID 688614(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 59610929HCID 59610929, compoundYield 83.7%

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-bromo-1-(4-bromophenyl)ethanone (3.6 g, 12.98 mmol) and (2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (2.0 g, 8.65 mmol) in MeCN (50 mL) was added Et3N (1.8 mL, 12.98 mmol). After 3 h, the solution was diluted with EtOAc, sat. NaHCO3, brine, dried over MgSO4, and concentrated. The residue was taken on crude to yield product (3.1 g).

Workup

  1. dry with materialdried over MgSO4
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-229a5e2aa3fd4b0f936fba63e618b32f
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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