Benzyl Bromide → phenylmethyl (2RS,3S)-3-amino-2-hydroxyheptanoate

To 13.1 g (50 mmol) of (2RS,3S)-2-hydroxy-3-[N-(2-methyl-2-propyloxycarbonyl)amino]heptanoic acid synthesized in accordance with the method described in Reference Example 11 and 100 ml of suspension of dimethylfomiamide of 6.3 g (75 mmol) of sodium hydrogen carbonate, 20 ml of dimethylformamide solution of 9.4 g (55 mmol) of benzyl bromide was added and stirred at the room temperature for 18 hours. The reaction solution was added with ethyl acetate and washed with water twice and washed with saturated brine once. The resultant organic extracted layer was dried over anhyrous sodium sulfate and then the solvent was distilled away under reduced pressure, whereby the crude product of phenylmethyl (2RS,3S)-2-hydroxy-3-[N-(2-methyl-2-propyloxycarbonyl) amino]heptanoate was obtained. To the obtained phenylmethyl (2RS,3S)-2-hydroxy-3-[N-(2-methyl-2-propyloxycarbonyl)amino]heptanoate, 100 ml of 4N hydrogen chloride-ethyl acetate were added and was left alone at room temperature for one hour and thereafter the reaction solution was concentrated under reduced pressure. The residue was dissolved in water and washed with diethyl ether twice and the water layer was made basic with addition of sodium carbonate and was extracted with ethyl acetate three times. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate and, the solvent was distilled away from the reaction mixture under reduced pressure, whereby 9.3 g of phenylmethyl (2RS,3S)-3-amino-2-hydroxyheptanoate was obtained.

1. additionwas added
2. washwashed with water twice
3. washwashed with saturated brine once
4. dry with materialThe resultant organic extracted layer was dried over anhyrous sodium sulfate
5. distillationthe solvent was distilled away under reduced pressure, whereby the crude product of phenylmethyl (2RS,3S)-2-hydroxy-3-[N-(2-methyl-2-propyloxycarbonyl) amino]heptanoate
6. customwas obtained
7. waitwas left alone at room temperature for one hour
8. concentrationthe reaction solution was concentrated under reduced pressure
9. dissolutionThe residue was dissolved in water
10. washwashed with diethyl ether twice
11. additionthe water layer was made basic with addition of sodium carbonate
12. extractionwas extracted with ethyl acetate three times
13. washThe organic layer was washed with saturated brine
14. dry with materialdried over anhydrous sodium sulfate
15. distillationthe solvent was distilled away from the reaction mixture under reduced pressure

ORD 기록

ord-867c43179c434af6a3a2a1ce68c3df61

출처 데이터셋

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06117870