Dimethylformamide → HCID 67351851, compound

HRID 1669527Notes

Reaction equation

HRID 1669527 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH3:29][O:30][C:31](=[O:49])[C@H:32]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=1)[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>O>[CH3:29][O:30][C:31](=[O:49])[C@@H:32]([NH:33][C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:6]=2)=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 7019130Boc-Tyr-OMeHCID 132544871-(2-Bromoethoxy)-4-phenoxybenzene

Product 1

HCID 67351851HCID 67351851, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-(2-Bromo-ethoxy)-4-phenoxy-benzene (2.5 g, 8.53 mmol), potassium carbonate (3.21 g, 23.3 mmol), and N,N-Dimethylformamide (150 mL) was added Boc-L-Tyrosine methyl ester (2.3 g, 7.75 mmol). The mixture was poured into 200 mL water solution and extracted with ethyl acetate (EtOAc) (3×100 mL). The combined organic layers were washed with brine (40 mL) and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo to obtain the crude mixture, which was purified by of silica gel flash chromatography, using EtOAc/hexane (gradient system), to obtain the product (2.54 g, 59%): 1H NMR (400 MHz, CDCL3).

Workup

  1. extractionextracted with ethyl acetate (EtOAc) (3×100 mL)
  2. washThe combined organic layers were washed with brine (40 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationThe organic layer was concentrated in vacuo
  5. customto obtain the crude mixture, which
  6. customwas purified by of silica gel flash chromatography

Sources & evidence

ORD record
ord-dd11fe90245c4cd6b725b34f3bd9d149
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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