反应详情

温度

-78 °C

DMSO (0.06 mL, 0.9 mmol) was added to a solution of oxalyl chloride (0.14 mL, 2.0 M, 0.28 mmol, in 4 ml, of methylene chloride) and the solution was then stirred for 10 minutes under a nitrogen atmosphere at −78° C. A solution of N-[(1-methylindole-2-carbonyl) valinyl]-3-amino-4-hydroxy-5-fluoropentanoic acid, t-butyl ester (85 mg, 0.18 mmol) in dry methylene chloride (1 mL), was added dropwise to the reaction mixture and the mixture was stirred for 15 minutes at −78° C. Triethylamine (0.15 ml, 1.08 mmol) was added dropwise to the reaction mixture and the mixture was stirred for 10 minutes at −78° C. and then was allowed to warm to room temperature. The reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution and the aqueous layer was back-extracted with ethyl acetate. The combined ethyl acetate solutions were washed with 5% KHSO4 solution and brine, dried over sodium sulfate, and concentrated to give a brown foam. The foam was triturated with ether to afford the title product as a light brown powder (64 mg). MS for C24H31ClFN3O5: (MH)−=494/496.

1. stirringthe mixture was stirred for 15 minutes at −78° C
2. stirringthe mixture was stirred for 10 minutes at −78° C.
3. temperatureto warm to room temperature
4. customThe reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution
5. extractionthe aqueous layer was back-extracted with ethyl acetate
6. washThe combined ethyl acetate solutions were washed with 5% KHSO4 solution and brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customto give a brown foam
10. customThe foam was triturated with ether