Hydrochloric Acid → 2-(4'-Methoxy-biphenyl-4-sulfonylamino)-3-methyl-butyric Acid Tert-butyl Ester

HRID 1292247Notes

Reaction equation

HRID 1292247 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(C)C=CC=CC=1.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(OCC)(=O)C>[C:1]([O:5][C:6](=[O:22])[CH:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 54389295HCID 54389295, compound

Product 1

HCID 702120142-(4'-Methoxy-biphenyl-4-sulfonylamino)-3-methyl-butyric Acid Tert-butyl Ester

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the 4-bromobenzenesulfonamide derivative (1 g, 2.64 mmol) prepared in Step (a) and 4-methoxybenzeneboronic acid (0.48 g, 3.17 mmol) in toluene (10 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (0.15 g, 0.1 mmol) and aqueous sodium carbonate (0.5 g/5 mL H2O), respectively. The reaction mixture was refluxed for 3 hours, then cooled to room temperature. Ethyl acetate (25 mL) and aqueous HCl (1M, 25 mL) were added, the layers separated, and the organic portion was dried (MgSO4), filtered, and the filtrate was concentrated in vacuo. The resulting solid was triturated with hexane/ethyl acetate (3:1) and was collected by filtration. Yield: 0.68 g (62%);

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customthe layers separated
  3. dry with materialthe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resulting solid was triturated with hexane/ethyl acetate (3:1)
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-fd540a544afe4430a7a3fb1ef779d0da
Source dataset
uspto-grants-1998_05
Patent number
US05756545

Reaction notes

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