2-Ethylhexanoic Acid → HCID 23665175, compound

HRID 1699536Notes

Reaction equation

HRID 1699536 reaction equation
C(OC([O:7][C@@H:8]([C@H:10]1[C:36](=[O:37])[N:12]2[C:13]([C:30]([O:32]CC=C)=[O:31])=[C:14]([CH2:17][N:18]3[N:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[S:19]3(=[O:29])=[O:28])[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+:67].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.ClCCl.C(OCC)(=O)C>[O:29]=[S:19]1(=[O:28])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[N:27][N:18]1[CH2:17][C:14]1[C@H:15]([CH3:16])[C@@H:11]2[C@@H:10]([C@H:8]([OH:7])[CH3:9])[C:36](=[O:37])[N:12]2[C:13]=1[C:30]([O-:32])=[O:31].[Na+:67]

Participants

9

Reactant 5

HCID 86972-Ethylhexanoic AcidHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 15908952HCID 15908952, compoundHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 23665175HCID 23665175, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The product from step 1 (29 mg, 0.055 mmol), triphenylphosphine (6.3 mg, 0.024 mmol), 0.5M sodium 2-ethyl-hexanoate in ethyl acetate (0.125 mL, 0.063 mmol), and 2-ethyl-hexanoic acid (0.0098 mL, 0.061 mmol) were dissolved in 1:1 dichloromethane-ethyl acetate (1 mL). Tetrakis(triphenylphosphine)palladium(0) (7 mg, 0.0061 mmol) was added and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was diluted with diethyl ether (7 mL) and extracted with water (2×1.5 mL). The aqueous extracts were washed with hexanes, concentrated under vacuum, and purified by preparative layer chromatography on a 1 mm×20 cm×20 cm RPSF plate, using 3:1 water-acetonitrile as the developing solvent. The product band was located by UV, removed and eluted with 4:1 acetonitrile-water. The eluent was concentrated under vacuum to remove the acetonitrile and lyophilized to afford the crude product (11 mg). This material was dissolved in ice cold water (1.5 mL) and applied to a small column of Amberchrom CG-161 resin (5 mm×5 cm). The column was eluted with cold water (20 mL) followed by 20% aqueous isopropanol in 2 mL fractions. The product containing, aqueous isopropanol fractions (2-7) were combined, concentrated under vacuum, and lyophilized to afford the title compound (5.6 mg) as an amorphous solid.

Workup

  1. extractionextracted with water (2×1.5 mL)
  2. washThe aqueous extracts were washed with hexanes
  3. concentrationconcentrated under vacuum
  4. custompurified by preparative layer chromatography on a 1 mm×20 cm×20 cm RPSF plate
  5. customremoved
  6. washeluted with 4:1 acetonitrile-water
  7. concentrationThe eluent was concentrated under vacuum
  8. customto remove the acetonitrile
  9. customto afford the crude product (11 mg)
  10. washThe column was eluted with cold water (20 mL)
  11. additionThe product containing
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5e688d68875a4e8a9302bb9a6e95bbd7
Source dataset
uspto-grants-2002_02
Patent number
US06346525B1

Reaction notes

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