反応 #640535

反応方程式

N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone

sodium borohydride

→

N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol

収率 43.0%

溶媒

methanol

tetrahydrofuran

反応条件

後処理

1. 1
   その他The solvents were removed under reduced pressure at 40° C.
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (approx. 1 L)
3. 3
   洗浄The solution was washed sequentially with 1M potassium hydrogen sulfate, saturated sodium bicarbonate
4. 4
   乾燥After drying over anhydrous magnesium sulfate
5. 5
   ろ過filtering
6. 6
   その他the solution was removed under reduced pressure
7. 7
   workup.ADDITIONTo the resulting oil was added hexane (approx. 1 L)
8. 8
   温度After cooling to room temperature
9. 9
   その他the solids were collected
10. 10
    洗浄washed with 2 L of hexane
11. 11
    その他The resulting solid was recrystallized from hot ethyl acetate and hexane

実験手順

To a solution of 75.0 g (0.226 mol) of N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone in a mixture of 807 mL of methanol and 807 mL of tetrahydrofuran at −2° C., was added 13.17 g (0.348 mol, 1.54 equiv.) of solid sodium borohydride over one hundred minutes. The solvents were removed under reduced pressure at 40° C. and the residue dissolved in ethyl acetate (approx. 1 L). The solution was washed sequentially with 1M potassium hydrogen sulfate, saturated sodium bicarbonate and then saturated sodium chloride solutions. After drying over anhydrous magnesium sulfate and filtering, the solution was removed under reduced pressure. To the resulting oil was added hexane (approx. 1 L) and the mixture warmed to 60° C. with swirling. After cooling to room temperature, the solids were collected and washed with 2 L of hexane. The resulting solid was recrystallized from hot ethyl acetate and hexane to afford 32.3 g (43% yield) of N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol, mp 150-151° C. and M+Li+=340.

出典