Sodium hydride → [3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid 2-(4-bromo-phenyl)-ethyl ester

温度

-40 °C

Sodium hydride (60% in oil, 60 mg, 1.5 mmol) was added portionwise to a solution of 4-bromophenethyl alcohol (0.718 g, 3.57) in THF (6 mL) at 0° C. The reaction mixture was cooled to −40° C., and a solution of 16G (0.550 g, 1.19 mmol) in THF (5 mL) was added slowly dropwise. The reaction mixture was slowly warmed to 0° C., and then stirred for 3 h at 0° C. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient from 0 to 50% ethyl acetate in hexanes) to give 16H (0.503 g, 74%) as a white solid.

1. temperatureThe reaction mixture was slowly warmed to 0° C.
2. extractionextracted with ethyl acetate
3. washThe combined organic layers were washed with water and brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica gel chromatography (gradient from 0 to 50% ethyl acetate in hexanes)
7. customto give 16H (0.503 g, 74%) as a white solid

ORDレコード

ord-340e5c48d0ea4b0aad8c746cca7b261e

出典データセット

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07592331B2