Diethyl Ether → HCID 57457956, compound

Temperature

5 °C

4.80 g (13.4 mmol) of methyltriphenylphosphonium bromide were added to a suspension of 1.41 g (12.6 mmol) of potassium t-butoxide in 100 ml of diethyl ether, and the resulting mixture was stirred for 15 minutes at 5° C. At the end of this time, a solution of 2.50 g (9.0 mmol) of (S)-1-benzyloxycarbonyl-4-oxoproline methyl ester in 30 ml of diethyl ether was added to the mixture thus obtained, and the mixture was stirred for an additional 3 hours at 35° C. At the end of this time, 50 ml of a saturated aqueous solution of ammonium chloride were added to the reaction mixture with ice-cooling, and the resulting mixture was partitioned. The organic extract thus obtained was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by chromatography on a silica gel column using a 1:3 by volume mixture of ethyl acetate and hexane as the eluant to afford 1.80 g (yield: 72%) of the title compound as a pale yellow oil.

1. customthus obtained
2. stirringthe mixture was stirred for an additional 3 hours at 35° C
3. temperaturecooling
4. customthe resulting mixture was partitioned
5. extractionThe organic extract thus
6. customobtained
7. washwas washed with water
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated by evaporation under reduced pressure
10. customThe residue was purified by chromatography on a silica gel column
11. additionby volume mixture of ethyl acetate and hexane as the eluant

ORD record

ord-68f09888b6cc4b64af1cecc8360eb43f

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07122666B2