Sodium Bicarbonate → HCID 69053516, compound

HRID 1866176Notes

Reaction equation

HRID 1866176 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:29])[CH2:9][NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Cl-].C[Zn+].[C:33](=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>[OH:29][C@H:8]([C:5]1[CH:6]=[N:7][C:2]([CH3:33])=[CH:3][CH:4]=1)[CH2:9][NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 86604899HCID 86604899, compoundHCID 178477797HCID 178477797, compound

Product 1

HCID 69053516HCID 69053516, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6049Ethylenediaminetetraacetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Under nitrogen to a solution of methyl 4′-[2-[[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]-1,1′-biphenyl-4-carboxylate (110 mg) in tetrahydrofran (10 ml) was added 1M methylzinc chloride in tetrahydrofran (0.8 ml) and tetrakis(triphenylphosphine)palladium (15.5 mg) at room temperature. The mixture was stirred at 80° C. for 24 hours, and then poured into an aqueous solution (60 ml) of ethylenediaminetetraacetic acid (1 g). The resulting mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=100:1) to give methyl 4′-[2-[[(2R)-2-hydroxy-2-(6-methyl-3-pyridyl)ethyl]amino]ethyl]-1,1′-biphenyl-4-carboxylate (41 mg) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-60efab2e4346438e8f32acc976e8190b
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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