反応 #1159155

反応方程式

BOC-O-benzyl-D-serine

SOCl2

MeOH

→

O-benzyl-D-serine methyl ester

反応条件

後処理

1. 1
   濃縮concentrated
2. 2
   洗浄washed with 10% Na2CO3 (3×80 mL)
3. 3
   乾燥The organic layer was dried over sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他To the crude material in EtOAc (100 mL) at 0° C. was bubbled HCl gas for approximately 10 minutes
7. 7
   その他the reaction was capped
8. 8
   workup.STIRRINGthe mixture stirred at 0° C. for 30 minutes before it
9. 9
   濃縮was concentrated in vacuo
10. 10
    workup.ADDITIONThe crude material was diluted with 50 mL of a 1:1 solution of saturated NaHCO3/10% Na2CO3
11. 11
    抽出extracted with EtOAc (4×50 mL)
12. 12
    乾燥The combined organics were dried over sodium sulfate
13. 13
    ろ過filtered
14. 14
    濃縮concentrated

実験手順

To a solution of BOC-O-benzyl-D-serine (5.05 g, 17.12 mmol) in MeOH (100 mL) at −78° C., was added SOCl2 dropwise. The reaction mixture was warmed to 0° C. and stirred for ˜4 hours and then concentrated. The residue was taken up in EtOAc and washed with 10% Na2CO3 (3×80 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. To the crude material in EtOAc (100 mL) at 0° C. was bubbled HCl gas for approximately 10 minutes, and the reaction was capped and the mixture stirred at 0° C. for 30 minutes before it was concentrated in vacuo. The crude material was diluted with 50 mL of a 1:1 solution of saturated NaHCO3/10% Na2CO3 and extracted with EtOAc (4×50 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give O-benzyl-D-serine methyl ester (3.13 g, 14.96 mmol) which was used without further purification. LCMS (ES) m/z 210.1 (M+H)+.

出典