反応 #621854

反応方程式

N-Boc-O-benzyl-D-serine

benzyl amine

→

solid

収率 50.0%

N-benzyl-O-benzyl-N2-Boc-D-serinamide

収率 50.0%

溶媒

tetrahydrofuran

N-methylmorpholine

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他reaction mixture
3. 3
   workup.ADDITIONisobutylchloformate (18 mL) was added to the reaction mixture in 5 minutes at −20° C
4. 4
   workup.STIRRINGThe solution was further stirred for 5 minutes at −20° C.
5. 5
   workup.STIRRINGThe solution was stirred for 1 hr at −20° C
6. 6
   workup.STIRRINGstirred for 1 hour
7. 7
   ろ過The precipitated hydrochloride salt of N-methylmorpholine was filtered
8. 8
   濃縮The filtrate was concentrated under vacuum

実験手順

To a cooled (−20° C.) solution of N-Boc-O-benzyl-D-serine (26 g) in tetrahydrofuran (208 mL), N-methylmorpholine (15 mL) was added and reaction mixture was stirred for 5 minutes. isobutylchloformate (18 mL) was added to the reaction mixture in 5 minutes at −20° C. The solution was further stirred for 5 minutes at −20° C. and benzyl amine (15.01 mL) was added to in it in 5 minutes at −20° C. The solution was stirred for 1 hr at −20° C. The solution was allowed to warm at room temperature and stirred for 1 hour. The precipitated hydrochloride salt of N-methylmorpholine was filtered. The filtrate was concentrated under vacuum to obtain solid 17 g N-benzyl-O-benzyl-N2-Boc-D-serinamide after crystallization from diisopropylether.

出典