2-Bromo-4'-nitroacetophenone → HCID 59396118, compound

HRID 1752535Notes

Reaction equation

HRID 1752535 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:19].C(N(C(C)C)CC)(C)C>C(#N)C.[Cl-].[Na+].O>[N:8]1([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([O:12][CH2:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)=[O:19])=[O:11]

Participants

6

Reactant 3

HCID 668402-Bromo-4'-nitroacetophenoneHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 59396118HCID 59396118, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of BOC-L-Proline (0.485 g, 2.25 mmol) and 2-Bromo-4′-nitro acetophenone (0.500 g, 2.05 mmol) in acetonitrile (20 mL) was added diisopropylethylamine (0.39 mL, 2.25 mmol) dropwise at ambient temperature. After stirred for four hours, the solution was poured into brine and extracted into ethyl acetate, dried over sodium sulfate, filtered, and the filtrate was concentrated to give a crude material that was used without purification (100% yield).

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0c7ed319b3054c128fefc6bd819af1dd
Source dataset
uspto-grants-2015_10
Patent number
US09163017B2

Reaction notes

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