反応 #48748

反応方程式

diisopropylethylamine

acetic anhydride

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

→

desired compound

収率 65.7%

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

収率 65.7%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGstir for 2 hours
2. 2
   その他Quench with aqueous 1N hydrochloric acid
3. 3
   洗浄wash with saturated aqueous sodium bicarbonate
4. 4
   乾燥dry with magnesium sulfate
5. 5
   その他purify on silica gel with dichloromethane/ethyl acetate

実験手順

Add acetic anhydride (0.142 mL, 1.51 mmol) to an ice cold solution of (2S,3S,5R)-5-[(1S,2S)-2-Amino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester (823 mg, 1.43 mmol) in dichloromethane (9 mL). Stir for 50 minutes and add diisopropylethylamine (0.125 mL, 0.717 mmol) and stir for 2 hours. Quench with aqueous 1N hydrochloric acid, wash with saturated aqueous sodium bicarbonate, dry with magnesium sulfate and purify on silica gel with dichloromethane/ethyl acetate mixtures to give the desired compound (493 mg). MS(ESI): m/z=525 [M+H]+.

出典