반응 #169621

반응 방정식

L-Alanine

NAD

pyridoxal-5-phosphate

sodium phosphate dibasic

(3S)-3-(benzyloxy)tetrahydro-4H-pyran-4-one

HCl

sodium formate

potassium carbonate

→

(3R,4S)-3-(benzyloxy)tetrahydro-2H-pyran-4-amine

용매

ethyl acetate

water

반응 조건

후처리

1. 1
   workup.DISSOLUTIONAfter all the components were completely dissolved
2. 2
   기타aged at 30° C
3. 3
   여과The mixture was filtered through a bed of Solka Floc
4. 4
   세척the cake was washed with ethyl acetate (250 mL)
5. 5
   기타The combined filtrates were separated
6. 6
   추출the aqueous layer was extracted a second time with ethyl acetate (2 L)
7. 7
   농축The combined organic extracts were concentrated in vacuo

실험 절차

To a solution of L-Alanine (200 g, 2.24 mol), sodium formate (76.0 g, 1.12 mmol), and sodium phosphate dibasic (28.7 g, 202 mmol) in 2.25 L of water adjusted to pH 7.5 was added NAD (2.2 g, 3.21 mmol), pyridoxal-5-phosphate (2.2 g, 8.90 mmol), LDH (0.45 g, 0.22 mol), FDH (4.5 g, 0.20 mol), and TA P1 G5 (4.5 g, 0.22 mol). After all the components were completely dissolved, (3S)-3-(benzyloxy)tetrahydro-4H-pyran-4-one (45 g, 0.22 mol) was added and the pH was adjusted to pH 7.25 with 6 N HCl and aged at 30° C. After 15 h, potassium carbonate (700 g, 5.06 mol) was added slowly, followed by ethyl acetate (2.2 L). The mixture was filtered through a bed of Solka Floc and the cake was washed with ethyl acetate (250 mL). The combined filtrates were separated and the aqueous layer was extracted a second time with ethyl acetate (2 L). The combined organic extracts were concentrated in vacuo to provide crude (3R,4S)-3-(benzyloxy)tetrahydro-2H-pyran-4-amine.

출처