반응 #640535

반응 방정식

N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone

sodium borohydride

→

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

수율 43.0%

용매

methanol

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

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