2-Ethylhexanoic Acid → HCID 23676231, compound

HRID 1699515Notes

Reaction equation

HRID 1699515 reaction equation
C(OC([O:7][C@@H:8]([C@H:10]1[C:40](=[O:41])[N:12]2[C:13]([C:34]([O:36]CC=C)=[O:35])=[C:14]([CH2:17][N:18]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][CH:27]=[C:28]5[CH:29]=[CH:30][CH:31]=[C:20]([C:21]=45)[S:19]3(=[O:33])=[O:32])[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+:71].C(OCC)(=O)C.C(C(CCCC)C(O)=O)C>C(OCC)C.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>[OH:7][C@@H:8]([C@H:10]1[C:40](=[O:41])[N:12]2[C:13]([C:34]([O-:36])=[O:35])=[C:14]([CH2:17][N:18]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][CH:27]=[C:28]5[CH:29]=[CH:30][CH:31]=[C:20]([C:21]=45)[S:19]3(=[O:32])=[O:33])[C@H:15]([CH3:16])[C@H:11]12)[CH3:9].[Na+:71]

Participants

8

Reactant 5

HCID 86972-Ethylhexanoic AcidHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 15542665HCID 15542665, compoundHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 23676231HCID 23676231, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

The product from step 1 (56 mg, 0.0961 mmol), triphenylphosphine (15 mg, 0.0577 mmol), 0.5M sodium 2-ethyl-hexanoate in ethyl acetate (0.211 mL, 0.106 mmol), 2-ethyl-hexanoic acid (0.0146 mL, 0.106 mmol), and tetrakis(triphenylphosphine)palladium(0) (22 mg, 0.0192 mmol) were combined in anhydrous dimethylfromamide (1 mL). The mixture was stirred at room temperature for 5 minutes, then cooled in an ice bath and stirred at 0-5° C. for 2 hours. The mixture was diluted with diethyl ether (12 mL) to precipitate a solid. The solid was collected by centrifugation, washed with ether (5 mL), and dried under vacuum. The solid was dissolved in water (5 mL) and added to a column (1×20 cm) of Amberchrom CG-161 resin. The column was eluted with water followed by a progressive gradient of acetonitrile in water. The product containing fractions were combined and lyophilized to a white, amorphous solid (18 mg). This material was further purified by preparative layer chromatography on a 1 mm×20 cm×20 cm RPSF plate, developing with 7:3 water-acetonitrile in an ice cooled tank. The product band was located by UV, removed and eluted with 4:1 acetonitrile-water. The eluent was washed with hexanes, filtered through a 0.45 micon disc, concentrated under vacuum to remove the acetonitrile, and lyophilized to afford the title compound (17.9 mg) as a white amorphous solid.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred at 0-5° C. for 2 hours
  3. customto precipitate a solid
  4. customThe solid was collected by centrifugation
  5. washwashed with ether (5 mL)
  6. customdried under vacuum
  7. dissolutionThe solid was dissolved in water (5 mL)
  8. additionadded to a column (1×20 cm) of Amberchrom CG-161 resin
  9. washThe column was eluted with water
  10. additionThe product containing fractions
  11. customThis material was further purified by preparative layer chromatography on a 1 mm×20 cm×20 cm RPSF plate
  12. customremoved
  13. washeluted with 4:1 acetonitrile-water
  14. washThe eluent was washed with hexanes
  15. filtrationfiltered through a 0.45 micon disc
  16. concentrationconcentrated under vacuum
  17. customto remove the acetonitrile

Sources & evidence

ORD record
ord-9386c3baea1e49808af39ef1bea13e76
Source dataset
uspto-grants-2002_02
Patent number
US06346526B1

Reaction notes

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