Реакция #215905

Уравнение реакции

Nα -(Benzyloxycarbonyl)-L-lysine

→

Nα -(benzyloxycarbonyl)-L-lysine tert-butyl ester

Выход 72.0%

Растворители

tert-butyl acetate

perchloric acid

Условия реакции

Обработка

1. 1
   Экстракцияwas extracted with water (3×200 ml)
2. 2
   ЭкстракцияThe aqueous solution was then extracted with ethyl acetate (3×200 ml)
3. 3
   Сушкаthe organic layers dried over MgSO4
4. 4
   ФильтрацияAfter filtration
5. 5
   Другоеto remove MgSO4
6. 6
   Другоеthe solvent was removed by evaporation at reduced pressure

Методика

Nα -(Benzyloxycarbonyl)-L-lysine (5.0 gm, 17.84 mmol) was dissolved in 268 ml of tert-butyl acetate containing 2.80 ml of perchloric acid (69-72% aqueous solution). The solution was stirred for 2 days at room temperature and then was extracted with water (3×200 ml). The combined aqueous layers were adjusted to pH 10 with 50% sodium hydroxide. The aqueous solution was then extracted with ethyl acetate (3×200 ml) and the organic layers dried over MgSO4. After filtration to remove MgSO4, the solvent was removed by evaporation at reduced pressure to provide Nα -(benzyloxycarbonyl)-L-lysine tert-butyl ester as a clear oil (2.16 gm, 36%). 1H NMR (CDCl3) 1.35 (s,9H), 1.40-2.0 (m,6H), 2.60 (t,2H), 4.10 (m, 1H), 4.98 (s,2H), 5.29 (bs,1H), 7.35 (s,5H).

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