Undecylenic Acid → HCID 72546827, compound

HRID 2280089Notes

Reaction equation

HRID 2280089 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]3[CH2:23][CH2:22][C:21](=[O:24])[C:9]3=[C:10]2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:41](O)(=[O:52])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH:50]=[CH2:51]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:41]([O:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([N:2]([CH3:25])[CH3:1])[CH:12]=3)[CH:7]=[C:8]3[CH2:23][CH2:22][C:21](=[O:24])[C:9]=23)=[CH:18][CH:17]=1)(=[O:52])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH:50]=[CH2:51]

Participants

6

Reactant 3

HCID 5634Undecylenic AcidHCID 10868DicyclohexylcarbodiimideHCID 72546580HCID 72546580, compound

Product 1

HCID 72546827HCID 72546827, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

An oven-dried, 25 mL one-necked round-bottomed flask was charged with compound 15b (0.021 g, 0.060 mmol), DCC (0.014 g, 0.069 mmol), DMAP (0.008 g, 0.069 mmol) and dry CH2Cl2 (7 mL). 10-Undecenoic acid (0.012 mL, 0.060 mmol) was added and the mixture was stirred at rt overnight. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 1:9). After filtration over a short pad of celite, the reaction was quenched with sat'd aq NaHCO3 solution (30 mL). The layers were separated and the aqueous phase was extracted with Et2O (3×15 mL). The combined organic layers were washed with brine (2×40 mL), dried over MgSO4, gravity filtered, and concentrated under reduced pressure. The reaction residue was purified by silica gel flash chromatography, eluting with AcOEt/n-hexane 1.5:8.5, to provide 0.018 g of the title compound as a yellow solid in 60% yield.

Workup

  1. customThe consumption of the starting material
  2. filtrationAfter filtration over a short pad of celite
  3. customthe reaction was quenched with sat'd aq NaHCO3 solution (30 mL)
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with Et2O (3×15 mL)
  6. washThe combined organic layers were washed with brine (2×40 mL)
  7. dry with materialdried over MgSO4, gravity
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe reaction residue was purified by silica gel flash chromatography
  11. washeluting with AcOEt/n-hexane 1.5:8.5

Sources & evidence

ORD record
ord-b3420566be24448b99363228c9d03d49
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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