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ChemicalBook CAS DataBase List Boc-L-serine methyl ester
2766-43-0

Boc-L-serine methyl ester synthesis

6synthesis methods
Di-tert-butyl dicarbonate

24424-99-5

L-Serine methyl ester hydrochloride

5680-80-8

Boc-L-serine methyl ester

2766-43-0

General procedure for the synthesis of Boc-L-serine methyl ester from di-tert-butyl dicarbonate and L-serine methyl ester hydrochloride: crude L-serine methyl ester hydrochloride (0.29 mol) was suspended in dichloromethane (200 mL), followed by the addition of triethylamine (79 mL, 0.57 mol) and di-tert-butyl dicarbonate (68 g, 0.31 mol) to the mixture. The reaction was carried out at 0°C. After removal of the cooling bath, the reaction mixture was stirred at room temperature overnight and then diluted with methyl tert-butyl ether (300 mL). The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by fast column chromatography on silica gel to afford Boc-L-serine methyl ester (60 g, 94% yield) as a colorless oil.

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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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