Dicyclohexylcarbodiimide → Phenyl-(R)-3-(2-Bromo-1-Oxooctyloxy)Tetradecanoate

HRID 327860

Reaktionsgleichung

Reaktionsgleichung von HRID 327860
[C:1]1([O:7][C:8](=[O:23])[CH2:9][C@H:10]([OH:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:24][CH:25]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:26](O)=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[C:1]1([O:7][C:8](=[O:23])[CH2:9][C@H:10]([O:22][C:26](=[O:27])[CH:25]([Br:24])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 552003Octanoic acid, 2-bromo-HCID 11726977phenyl-(R)-3-hydroxytetradecanoate

Produkt 1

HCID 11016835Phenyl-(R)-3-(2-Bromo-1-Oxooctyloxy)TetradecanoateAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1.02 g phenyl-(R)-3-hydroxytetradecanoate (3.19 mmol), 22 mL dichloromethane, 0.74 g 2-bromooctanoic acid (3.19 mmol), 0.66 g N,N'-dicyclohexylcarbodiimide (3.20 mmol) and 0.39 g 4-dimethylaminopyridine (3.19 mmol) was stirred at room temperature for 1.5 hours. The solution was then concentrated to dryness on a rotary evaporator (ca. 26 mm Hg, 30° C.). 25 mL hexanes was added to the white powdery residue and the resultant mixture was stirred at room temperature for 5 minutes. The slurry was filtered through a coarse sintered glass funnel and the solids were washed with 2×20 mL hexanes. The combined filtrates were placed in a separatory funnel and washed with 2×50 mL 1M HCL, 2×50 mL 10% saturated sodium bicarbonate and 2×50 mL city water. The organic layer was dryed over magnesium sulfate, then gravity filtered through paper, and concentrated on a rotary evaporator (ca. 10 mm Hg, 30° C.). The residue was chromatographed on a 2' by 1" column slurry packed with silica gel (80 g) in hexanes. Product was eluted with 50/50 hexanes and dichloromethane. The chromatography was monitored by TLC (silica gel, 50/50 hexanes: dichloromethane, phosphomolybidic acid visualization). Fractions containing only product were pooled and concentrated on a rotary evaporator (ca. 100 mm Hg, 30° C.). A cloudy oil (0.98 g, 58% yield) was obtained.

Aufarbeitung

  1. concentrationThe solution was then concentrated to dryness on a rotary evaporator (ca. 26 mm Hg, 30° C.)
  2. addition25 mL hexanes was added to the white powdery residue
  3. stirringthe resultant mixture was stirred at room temperature for 5 minutes
  4. filtrationThe slurry was filtered through a coarse sintered glass funnel
  5. washthe solids were washed with 2×20 mL hexanes
  6. customThe combined filtrates were placed in a separatory funnel
  7. washwashed with 2×50 mL 1M HCL, 2×50 mL 10% saturated sodium bicarbonate and 2×50 mL city water
  8. filtrationgravity filtered through paper
  9. concentrationconcentrated on a rotary evaporator (ca. 10 mm Hg, 30° C.)
  10. customThe residue was chromatographed on a 2' by 1" column slurry
  11. washProduct was eluted with 50/50 hexanes and dichloromethane
  12. additionFractions containing only product
  13. concentrationconcentrated on a rotary evaporator (ca. 100 mm Hg, 30° C.)

Quellen und Nachweise

ORD-Eintrag
ord-9d2a0fc31ce04aafa71fa3e1631d175b
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274143

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