Diethyl Ether → HCID 23508244, compound

HRID 413405Notes

Reaction equation

HRID 413405 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH2:19])[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.CCOCC>C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].O.CO.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>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:2]2[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH:12]([CH:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=[CH2:19])[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:6][CH:7]=2)=[CH:32][CH:31]=1

Participants

9

Reactant 3

HCID 3283Diethyl EtherHCID 201262(4-Methoxyphenyl)boronic acidHCID 23508255Methyl 2-[4-bromophenylsulfonyl]amino-3-phenylmethoxy-4-pentenoate

Product 1

HCID 23508244HCID 23508244, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

The methyl 2-[4-bromophenylsulfonyl]amino-3-phenylmethoxy-4-pentenoate 63c (320 mg, 0.683 mmol) is dissolved in benzene (4 mL) and sodium carbonate (148 mg), in water (0.6 mL), is added along with tetrakis(triphenylphosphine)palladium. 4-Methoxyphenylboronic acid (157 mg, 1.03 mmol), in methanol (0.4 mL), is added and the mixture is heat to reflux overnight. Ether is added to the reaction which is washed with water (3 times) and brine, the organic layer is dried over magnesium sulfate and the solvent stripped in vacuo to give the crude product as a yellow solid. The crude material is adsorbed onto silica gel and purified over a silica column eluting with hexane/ethyl acetate (9:1) followed with hexane/ethyl acetate (1/1). Product fractions are combined and dried to give the desired product.

Workup

  1. temperaturethe mixture is heat
  2. temperatureto reflux overnight
  3. washis washed with water (3 times) and brine
  4. dry with materialthe organic layer is dried over magnesium sulfate
  5. customto give the crude product as a yellow solid
  6. custompurified over a silica column
  7. washeluting with hexane/ethyl acetate (9:1)
  8. customdried

Sources & evidence

ORD record
ord-d5efb9a9c8894b0e82c5778a6053f8fe
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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