Potassium Carbonate → HCID 131724970, compound

HRID 1070434Notes

Reaction equation

HRID 1070434 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([O:20][CH3:21])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[K+].[K+].F[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N+:35]([O-:37])=[O:36]>CN(C)C=O.CCOCC>[C:1]([NH:8][C@H:9]([C:18]([O:20][CH3:21])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N+:35]([O-:37])=[O:36])=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 7019130Boc-Tyr-OMe

Product 1

HCID 131724970HCID 131724970, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-Boc-(L)tyrosine, methyl ester (500 mg) and potassium carbonate (467 mg) in dimethylformamide (5 mL) was added dropwise 1-fluoro-2-nitrobenzene (189 μL). The yellow solution was stirred for 3 days at room temperature. The mixture was diluted with ether which was subsequently washed with 1N hydrochloric acid, water, saturated salt solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by rotoevaporation to yield the title compound (700 mg) which was used in the subsequent reaction without further purification.

Workup

  1. washwas subsequently washed with 1N hydrochloric acid, water, saturated salt solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was removed by rotoevaporation

Sources & evidence

ORD record
ord-6ec179a87e8b43328d912c40a5e7dd18
Source dataset
uspto-grants-2005_06
Patent number
US06903075B1

Reaction notes

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