Sodium Carbonate → Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-2-nitro-4-biphenylcarboxylate

HRID 2220394Notes

Reaction equation

HRID 2220394 reaction equation
[CH2:1]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:27]([C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=1OS(C(F)(F)F)(=O)=O)[C:33]([O:35][CH3:36])=[O:34])([O-:29])=[O:28].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.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>[CH2:1]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:39]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=2[N+:27]([O-:29])=[O:28])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 10925511Methyl 3-nitro-4-[[(trifluoromethyl)sulfonyl]oxy]benzoateHCID 22171360(4-[2-[Benzyl(tert-butoxycarbonyl)amino]ethyl]phenyl]boronic acid

Product 1

HCID 69104049Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-2-nitro-4-biphenylcarboxylateYield 71.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [4-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]phenyl]boronic acid (3.1 g) in 1,2-dimethoxyethane (45 ml) were added methyl 3-nitro-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate (3.0 g), tetrakis(triphenylphosphine)palladium (800 mg) and aqueous solution of sodium carbonate (2M, 9.1 ml), and the mixture was stirred at 80° C. for 4 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-2-nitro-4-biphenylcarboxylate (3.05 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-a729ae6c697149a38d30fc19474baa3c
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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