反応 #48751

反応方程式

acetic anhydride

(2R,5R)-5-[(1S,2S)-2-amino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-2-(2-fluoro-1-fluoromethyl-1-methyl-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester

triethylamine

→

desired compound

収率 89.9%

(2R,5R)-5-[(1S,2S)-2-acetylamino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-2-(2-fluoro-1-fluoromethyl-1-methyl-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester

収率 89.9%

溶媒

dichloromethane

反応条件

後処理

1. 1
   濃縮Concentrate under reduced pressure
2. 2
   洗浄eluting with 40:60 to 0:100 hexane/ethyl acetate gradient

実験手順

Add acetic anhydride (2.13 mmoles; 201.52 μL) to a solution of (2R,5R)-5-[(1S,2S)-2-amino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-2-(2-fluoro-1-fluoromethyl-1-methyl-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester (2.03 mmoles; 1.00 g) and triethylamine (2.23 mmoles; 311.29 μL) in 10 mL dichloromethane at 0° C. (ice bath) and stir the mixture at 0° C. for 1 h. Concentrate under reduced pressure and subject residue to silica gel chromatography eluting with 40:60 to 0:100 hexane/ethyl acetate gradient to give the desired compound as white solid (950.00 mg, 87.53%).

出典