2-Ethylhexanoic Acid → HCID 23703464, compound

HRID 1597170Notes

Reaction equation

HRID 1597170 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:31]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[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>ClCCl.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>[O:33]=[S:19]1(=[O:32])[N:18]([CH2:17][C:14]2[C@H:15]([CH3:16])[C@@H:11]3[C@@H:10]([C@H:8]([OH:7])[CH3:9])[C:40](=[O:41])[N:12]3[C:13]=2[C:34]([O-:36])=[O:35])[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2.[Na+:71]

Participants

9

Reactant 5

HCID 86972-Ethylhexanoic AcidHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 15536007HCID 15536007, compoundHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 23703464HCID 23703464, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The product from step 1 (22 mg, 0.038 mmol) in dichloromethane (0.5 mL) was treated with triphenylphosphine (1.6 mg, 0.0061 mmol), 0.5M sodium 2-ethyl-hexanoate in ethyl acetate (0.021 mL, 0.011 mmol), 2-ethyl-hexanoic acid (0.007 mL, 0.044 mmol) and tetrakis(triphenylphosphine)palladium(0) (4.4 mg, 0.0038 mmol). The mixture was stirred at room temperature for 15 minutes, then diluted with ethyl ether (5 mL) and centrifuged. The solid pellet was washed with ether (1.5 mL), taken up in 20% acetonitrile in water (3 mL), and applied to a column of Bio-Rad Macro-Prep CM weak cation exchange resin (2 mL). The column was eluted with 20% acetonitrile in water. The product containing fractions were concentrated under vacuum and lyophilized to afford the title compound (13.4 mg) as an amorphous solid.

Workup

  1. washThe solid pellet was washed with ether (1.5 mL)
  2. washThe column was eluted with 20% acetonitrile in water
  3. additionThe product containing fractions
  4. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-9d8ba773788e4100938fb7ed34ef33f0
Source dataset
uspto-grants-2001_09
Patent number
US06294528B1

Reaction notes

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