N,N-Dimethylglycine → HCID 67351665, compound

HRID 1669518Notes

Reaction equation

HRID 1669518 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Br[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 7806p-BromochlorobenzeneHCID 10796Cesium carbonateHCID 7019130Boc-Tyr-OMe

Product 1

HCID 67351665HCID 67351665, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-2-tert-Butoxycarbonylamino-3-[4-hydroxy-phenyl]-propionic acid methyl ester (2 g, 6.8 mmol, 1 eq.) in dioxane (20 ml) was added 4-bromochlorobenzene (1.95 g, 10 mmol, 1.5 eq.), CuI(I) (140 mg, 0.7 mmol, 0.1 eq.), N,N-dimethylglycine (220 mg, 2.1 mmol, 0.3 eq.) and cesium carbonate (4.6 g, 14 mmol, 3 eq.). The resulting mixture was stirred under Ar at reflux overnight. After cooling to room temperature, the volatile material was removed under reduced pressure to give a residue, which was partitioned between water and ethyl acetate. The ethyl acetate layer was separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The combined ethyl acetate layers were dried over anhydrous MgSO4. Evaporation of solvent under reduced pressure gave a residue, which was purified by chromatography on silica gel using dichloromethane/MeOH (50:1) as eluent to give the desired product (587 mg, 21% yield).

Workup

  1. temperatureat reflux overnight
  2. customthe volatile material was removed under reduced pressure
  3. customto give a residue, which
  4. customwas partitioned between water and ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (2×20 ml)
  7. dry with materialThe combined ethyl acetate layers were dried over anhydrous MgSO4
  8. customEvaporation of solvent under reduced pressure
  9. customgave a residue, which
  10. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8f37cf245f1a46f99ba090785d205c23
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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