Toluene → HCID 10222746, compound

Acid 18a (927 mg, 3.26 mmol) was stirred in oxalyl chloride (5 mL) at room temperature for 2 minutes and dry toluene (4 mL) was added to facilitate stirring. After 1 h, the mixture was concentrated. Ethanol (10 mL) and triethylamine (1.35 mL) were added and the dark yellow mixture was stirred overnight. The mixture was then concentrated and partitioned between ethyl acetate (25 mL) and water (25 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (10 mL). The combined organic layers were washed with water (20 mL) and the combined aqueous layers were extracted with ethyl acetate (20 mL). The combined organic layers were dried with Na2SO4, filtered, and concentrated to yield 18c as an oil. Purification by flash chromatography (4/1 CH2Cl2/MeOH) yielded 18c (136 mg) as a yellow oil. The structure was confirmed by 1H NMR and LC/MS. (Esters 18d, 18e, and 18f were similarly prepared.)

1. concentrationthe mixture was concentrated
2. additionEthanol (10 mL) and triethylamine (1.35 mL) were added
3. stirringthe dark yellow mixture was stirred overnight
4. concentrationThe mixture was then concentrated
5. custompartitioned between ethyl acetate (25 mL) and water (25 mL)
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with ethyl acetate (10 mL)
8. washThe combined organic layers were washed with water (20 mL)
9. extractionthe combined aqueous layers were extracted with ethyl acetate (20 mL)
10. dry with materialThe combined organic layers were dried with Na2SO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-d57fcbd89a824cdf83f5d427ef2cec47

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07317026B2