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

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.

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.)

ORDレコード

ord-25de7aea0ebc4aa88c84c7802bd3c03b

出典データセット

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05420305