Triethylamine → HCID 69113061, compound

HRID 989505Notes

Reaction equation

HRID 989505 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]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.S(=O)(=O)(O)[O-].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:25]([O:24][C:20](=[O:23])[CH:21]=[CH:22][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)[CH3:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 11784171(+,-) Trans Propane-2-sulfonic Acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 69113061HCID 69113061, compoundYield 45.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 516919Sodium BisulfateSolvent

Conditions

Temperature
80 °C

Procedure

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (150 mg, 0.38 mmol, prepared in example 2) was dissolved in DMF (5.0 mL) and ethyl acrylate (103 uL, 0.95 mmol), triethylamine (186 uL, 1.3 mmol), palladium acetate (4 mg, 0.02 mmol), and triphenylphosphine (10 mg, 0.04 mmol) were added. The reaction was heated to 80° C. and stirred overnight under nitrogen. Allowed the reaction to cool and diluted with 75 mL of 10% aqueous sodium bisulfate and extracted into methylene chloride (2×50 mL). Dried the organics over sodium sulfate, filtered and concentrated in vacuo to a crude brown oil. The desired compound was purified by radial chromatography eluting with methylene chloride followed by the addition of 2% MeOH. The appropriate fractions were concentrated to provide 63 mg (45%) of a near-colorless oil of the title compound.

Workup

  1. customAllowed the reaction
  2. temperatureto cool
  3. extractionextracted into methylene chloride (2×50 mL)
  4. dry with materialDried the organics over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a crude brown oil
  7. customThe desired compound was purified by radial chromatography
  8. washeluting with methylene chloride
  9. additionfollowed by the addition of 2% MeOH
  10. concentrationThe appropriate fractions were concentrated

Sources & evidence

ORD record
ord-e408f7e8f8714ca99fed941b12982997
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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