Potassium Carbonate → (+,-) Trans Propane-2-sulfonic Acid (2-biphenyl-4-yl-cyclopentyl)-amide

HRID 989487Notes

Reaction equation

HRID 989487 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 11784171(+,-) Trans Propane-2-sulfonic Acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 12144739(+,-) Trans Propane-2-sulfonic Acid (2-biphenyl-4-yl-cyclopentyl)-amideYield 68%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Conditions

Temperature
90 °C

Procedure

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (58 mg, 0.15 mmol, prepared in example 2) and phenylboronic acid (22 mg, 0.18 mmol) were dissolved in 20 mL of n-propanol and 25 mg (0.18 mmol)of potassium carbonate in 5 mL of water added. A catalytic amount of palladium acetate is added (2 mg) and the mixture refluxed at 90° C. for 4 hours. The reaction is filtered, rinsed with ethyl acetate. The filtrate is diluted with ethyl acetate and washed with saturated sodium bicarbonate (3×30 mL) and brine (1×30 mL). The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo to a crude solid which is purified by reverse phase chromatography (Vydac C18 column with a CH3CN gradient of 5→55% over 2 hours with a flow rate of 20 mL/min). The fractions were freeze-dried to give 34 mg (68%) of the title compound. The NMR was consistent with. the assigned structure.

Workup

  1. filtrationThe reaction is filtered
  2. washrinsed with ethyl acetate
  3. additionThe filtrate is diluted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate (3×30 mL) and brine (1×30 mL)
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a crude solid which
  8. customis purified by reverse phase chromatography (Vydac C18 column with a CH3CN gradient of 5→55% over 2 hours with a flow rate of 20 mL/min)
  9. customThe fractions were freeze-dried

Sources & evidence

ORD record
ord-85a7158ed7b94a7bb0e748148cc4dd7e
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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