反应详情

温度

-78 °C

DMSO (0.13 mL, 1.9 mmol) was added to a methylene chloride solution of oxalyl chloride (0.29 mL, 2.0M, 0.58 mmol in 4 mL of methylene chloride), and the resultant solution was stirred for 10 minutes under a nitrogen atmosphere at 78° C. A methylene chloride solution of N-[(1-phenylindole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-fluoropentanoic acid, t-butyl ester (200 mg, 0.38 mmol in 2 mL of dry methylene chloride) was added dropwise and resulting mixture stirred for 15 minutes at -78° C. Triethylamine (0.30 mL, 2.1 mmol) was added dropwise to the mixture, and the resultant mixture was stirred for 10 minutes at -78° C., 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 crude product. The crude product was triturated to yield the title product as a slightly yellow powder (181 mg). TLC: (ethyl acetate/hexanes 1:1): Rf =0.43.

1. customresulting mixture
2. temperatureto warm to room temperature
3. customThe reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution
4. extractionthe aqueous layer was back-extracted with ethyl acetate
5. washThe combined ethyl acetate solutions were washed with 5% KHSO4 solution and brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customto give a crude product
9. customThe crude product was triturated