Sodium 2-ethylhexanoate → HCID 57617740, compound

HRID 1670425Notes

Reaction equation

HRID 1670425 reaction equation
[OH:1][C@@H:2]1[C@H:6]([C@H:7]([OH:14])/[CH:8]=[CH:9]/[C:10]([CH3:13])([CH3:12])[CH3:11])[O:5][C:4](=[O:15])[C@@H:3]1[O:16][CH3:17].Cl.[NH2:19][C@@H:20]1[C:26](=[O:27])[N:25]([CH2:28][CH3:29])[C:24]2[CH:30]=[CH:31][CH:32]=[CH:33][C:23]=2[O:22][CH2:21]1.C(C(CCCC)C([O-])=O)C.[Na+]>C1COCC1>[CH2:28]([N:25]1[C:24]2[CH:30]=[CH:31][CH:32]=[CH:33][C:23]=2[O:22][CH2:21][C@H:20]([NH:19][C:4](=[O:15])[C@H:3]([O:16][CH3:17])[C@H:2]([OH:1])[C@@H:6]([OH:5])[C@H:7]([OH:14])/[CH:8]=[CH:9]/[C:10]([CH3:13])([CH3:12])[CH3:11])[C:26]1=[O:27])[CH3:29]

Participants

5

Reactant 3

HCID 23672331Sodium 2-ethylhexanoateHCID 57617720HCID 57617720, compoundHCID 67327839HCID 67327839, compound

Product 1

HCID 57617740HCID 57617740, compoundYield 217.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

181 mg of 2 (742 μmol), 180 mg of 20 (742 μmol) and 296 mg of sodium 2-ethylhexanoate (1.78 mmol) in 3 mL of THF are successively introduced into a 25 mL round-bottomed flask, with stirring and under an argon atmosphere. The stirring is maintained at RT for 24 h. The mixture is concentrated and 727 mg of crude product are obtained, which product is chromatographed on a silica cartridge [50 g, eluent heptane/AcOEt-heptanel (50/50), in an AcOEt-heptane (50/50) gradient: 0 to 100%]. 177 mg of expected product Ex9 are recovered.

Workup

  1. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-407bd7b7875d430b8b40cec66c1874f1
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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