反応 #1063205

反応方程式

(S)-4-amino-2-tert-butyloxycarbonylaminobutyric acid

→

(S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-azaoctanedioic acid

溶媒

acetonitrile

acetonitrile

反応条件

後処理

1. 1
   その他degassed H2O (50 ml)
2. 2
   温度The pH was maintained at 5.5 by dropwise addition of 1M NaHCO3
3. 3
   workup.STIRRINGThe mixture was stirred for 5 days at ambient temperature
4. 4
   workup.ADDITIONThe pH was controlled by NaHCO3 addition
5. 5
   workup.DISTILLATIONThe solvents were distilled off
6. 6
   その他the residue triturated with chloroform (5 ml), to which acetic acid
7. 7
   workup.ADDITIONwas added
8. 8
   その他to give pH 5
9. 9
   その他The chloroform solution was evaporated
10. 10
    その他the product isolated after chromatography on silica gel (CHCl3:MeOH 2:1)

実験手順

A solution of (S)-4-amino-2-tert-butyloxycarbonylaminobutyric acid (1.03 g, 4.70 mmol) in acetonitrile (50 ml) was added to a solution of (S)-Boc-serine-β-lactone (0.80 g, 4.27 mmol) in acetonitrile (50 ml) and degassed H2O (50 ml). The pH was maintained at 5.5 by dropwise addition of 1M NaHCO3 with stirring. The mixture was stirred for 5 days at ambient temperature. The pH was controlled by NaHCO3 addition and the reaction monitored by TLC. The solvents were distilled off, the residue triturated with chloroform (5 ml), to which acetic acid was added to give pH 5. The chloroform solution was evaporated and the product isolated after chromatography on silica gel (CHCl3:MeOH 2:1).

出典