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ChemicalBook CAS DataBase List Boc-L-serine methyl ester

Boc-L-serine methyl ester synthesis

6synthesis methods
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Yield:2766-43-0 93%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20; for 4.5 h;Cooling with ice;

Steps:

N-(tert-Butoxycarbonyl)-L-serine methyl ester (5)
To a solution of 4 (1.26 g, 6.1 mmol) and potassiumcarbonate (0.91 g, 6.6 mmol) in DMF (12 mL) cooled on an ice bath was added a solution of iodomethane (0.80mL, 12.8 mmol) in DMF (6 mL). After stirring for 30 min on an ice bath, the mixture was stirred for 4 h at rt.Precipitates were filtered off, and the filtrate was added with water and extracted with EtOAc. The organiclayer was washed with water and brine, dried over MgSO4, and evaporated. The obtained colorless oil waspurified by silica gel column chromatography (hexane:EtOAc = 1:1) to give 5 as a colorless oil (1.24 g, 93%).The spectral data of 5 were identical to the literature,25 and the purity was confirmed by 1H NMR.

References:

Shimodaira, Shingo;Iwaoka, Michio [Arkivoc,2016,vol. 2017,# 2,p. 260 - 271]

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