Oleic Acid → HCID 86682232, compound

HRID 1479322Notes

Reaction equation

HRID 1479322 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][OH:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[C:15]([OH:34])(=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].Cl.C(N=C=N[CH2:41][CH2:42][CH2:43]N(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:15]([O:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][O:14][C:15](=[O:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])(=[O:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:43][CH2:42][CH3:41]

Participants

6

Reactant 3

HCID 445639Oleic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4360601N-Boc-diethanolamine

Product 1

HCID 86682232HCID 86682232, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl bis(2-hydroxyethyl)carbamate (Aldrich; 600 mg, 2.92 mmol) was dissolved in dichloromethane (30 mL), and stirred overnight at room temperature after adding oleic acid (Tokyo Chemical Industry Co., Ltd.; 1.82 g, 6.43 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.29 g, 6.72 mmol), and 4-dimethylaminopyridine (89 mg, 0.731 mmol). The aqueous layer was extracted with ethyl acetate after adding a saturated sodium bicarbonate aqueous solution to the reaction mixture. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100) to give tert-butyl N,N-bis(2-((Z)-octadec-9-enoyloxy)ethyl)carbamate (1.26 g, 58.7%).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. additionafter adding a saturated sodium bicarbonate aqueous solution to the reaction mixture
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationafter filtration
  7. customThe resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100)

Sources & evidence

ORD record
ord-b3717de83ba8407183f7c9c86dc9a936
Source dataset
uspto-grants-2016_08
Patent number
US09408914B2

Reaction notes

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