Cesium carbonate → HCID 21137722, compound

HRID 1358580Notes

Reaction equation

HRID 1358580 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:20]C1C=CC(O)=CC=1)[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].C(=O)([O-])[O-:39].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH3:20])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:39][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:8][C:7]=1[C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 10667178N-(2-benzoylphenyl)tyrosine methyl ester

Product 1

HCID 21137722HCID 21137722, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-(2-benzoylphenyl)tyrosine methyl ester (0.97 g), t-butyl bromoacetate (0.55 ml), cesium carbonate (1.14 g), and acetone (15 ml) was stirred at room temperature for 1.5 hours and allowed to stand overnight. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the title compound (1.42 g, Rf=0.65: thin layer chromatography on a silica gel plate using hexane: ethyl acetate=3:1 as the eluant).

Workup

  1. waitto stand overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe extract was washed with saturated aqueous chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1963ac32b3a04352b8a8fc389959067b
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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