Methanol → HCID 44201124, compound

HRID 1486472Notes

Reaction equation

HRID 1486472 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1CCC(N=C=NC2CCCCC2)CC1.CO.[NH2:38][C@H:39]([CH2:43][OH:44])[CH:40]([CH3:42])[CH3:41]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([NH:38][C@H:39]([CH2:43][OH:44])[CH:40]([CH3:42])[CH3:41])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 445639Oleic AcidHCID 640993L-Valinol

Product 1

HCID 44201124HCID 44201124, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a round bottom flask, oleic acid (1) (1.53 g, 5.33 mmol) was dissolved in 20 ml of dry pyridine (over KOH). To the solution TEA (0.74 ml, 5.33 mmol), DCC (1.1 g, 5.33 mmol), and NHS (0.55 g, 4.85 mmol) were added. The mixture was stirred at room temperature for overnight. After confirming the total conversion of the acid to the NHS intermediate using TLC (5% MeOH), L-Valinol (0.5 g, 4.85 mmol) was added and the mixture was stirred for additional 24 hours. After completion of the reaction (TLC: 100% Ethyl acetate), volatiles were removed under reduced pressure to dryness. The gum was dissolved in 5 ml DCM and the desired product oleoyl-valinol (10) was obtained using column chromatography (dichloromethane/ethyl acetate=1:1, v/v)). Colorless viscous oil (0.94 g, 46.8 yield).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for additional 24 hours
  3. customwere removed under reduced pressure to dryness
  4. dissolutionThe gum was dissolved in 5 ml DCM

Sources & evidence

ORD record
ord-58c7b81487564db6ab101db74a1ebf5c
Source dataset
uspto-grants-2016_08
Patent number
US09428448B2

Reaction notes

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