Propyl mercaptan → HCID 18723452, compound

Temperature

-78 °C

To a cooled (−78° C.) solution of 5.7 g (75.0 mmol) of propanethiol in 250 mL THF was added 34.4 mL n-butyllithium (1.6M, 55.0 mmol) and the solution was stirred for 45 min at −78° C. under nitrogen and then warmed to −10° C. To the resulting white suspension was added a solution of 9.6 g (22.0 mmol) of (S)-N-[(1-Benzyl)-4-(R)-(ethoxycarbonyl)-3-(S)-pyrrolidinylcarbonyl]-4-benzyl-2-oxazolidinone in 250 mL THF. The reaction was stirred for 30 min and then removed from the bath and allowed to warm to rt over 1 h. The clear solution was partitioned between 1.5 L of ether and 500 mL of 1M NaOH and the layers were separated. The aqueous layer was washed with ether and the combined organic fractions were washed with sat'd NCl solution, dried over MgSO4, filtered, and the filtrate was concentrated.

1. temperaturewarmed to −10° C
2. stirringThe reaction was stirred for 30 min
3. customremoved from the bath
4. temperatureto warm to rt over 1 h
5. customThe clear solution was partitioned between 1.5 L of ether and 500 mL of 1M NaOH
6. customthe layers were separated
7. washThe aqueous layer was washed with ether
8. washthe combined organic fractions were washed with sat'd NCl solution
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationthe filtrate was concentrated

ORD record

ord-aaa181a1aea84806b5aca5b48ab8128c

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06372764B1