Potassium Carbonate → HCID 10126493, compound

HRID 852250Notes

Reaction equation

HRID 852250 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](OS(C(F)(F)F)(=O)=O)=[CH:8][CH:7]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O>[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30][CH3:29])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 10455198(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

Product 1

HCID 10126493HCID 10126493, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

(S)-2-tert-Butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxyphenyl) propionic acid methyl ester (1.88 g, 4.39 mmol, prepared as described in Preparation 23, was dissolved in glyme (58 ml) and water (4 ml). To this solution 2-methoxyphenylboronic acid (2.0 g, 13.16 mmol), tetrakistriphenylphosphine palladium (0) (2.79 g, 2.41 mmol) and potassium carbonate (2.12 g, 15.37 mmol) were added. The reaction mixture was degassed and then heated at 80° C. for 6 h. The mixture was diluted with EtOAc (100 ml), washed with saturated aqueous NaHCO3 (100 ml) and brine (100 ml) and dried over MgSO4. The mixture was filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (9:1 to 4:1 hexanes/EtOAc) to give (S)-2-tert-butoxycarbonylamino-3-(2′-methoxy-biphenyl-4-yl)-propionic acid methyl ester (1.1 g, 65%) as a white solid.

Workup

  1. customas described in Preparation 23
  2. customThe reaction mixture was degassed
  3. additionThe mixture was diluted with EtOAc (100 ml)
  4. washwashed with saturated aqueous NaHCO3 (100 ml) and brine (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography over silica gel (9:1 to 4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-6f32b43e7f7747c1bb1fc9518c9d38d7
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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