2766-43-0 Tert-butoxycarbonyl-L-serine-methyl ester

Synonyms

Boc-L-serine methyl ester;
BOC-L-SERINE METHYL ESTER;
BOC-SERINE-OME;BOC-SER-OME;
N-ALPHA-T-BUTOXYCARBONYL-L-SERINE METHYL ESTER;
N-BOC-L-SERINE METHYL ESTER;
N-(TERT-BUTOXYCARBONYL)-L-SERINE METHYL ESTER;
Butoxycarbonylserinemethylester;
N-T-BOC-L-SERINE METHYL ESTER

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Applications

Boc-L- Serine methyl ester can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.
3.1Kg l-serine was dissolved in 30L methanol, then 2.2L sulfoxide chloride was added at room temperature, stirring for 2h and then heating for reflux for 8 hours. The reaction solution was concentrated and dried. The concentrated solution was dissolved in 30L methylene chloride, and 9.2L triethylamine and 7.25kg di-tert-butyl dicarbonate were added. The reaction solution was washed with 1N sodium bisulfate solution, 5% sodium bicarbonate solution, 10% citric acid and saturated salt water. The organic phase was dried with anhydrous sodium sulfate. The solvent was removed under pressure to obtain compound Ⅰ6.38kg with a yield of 94%.
The crude (5)-methyl 2-amino-3-hydroxypropanoate hydrochloride (0.29 mol) was suspended in DCM (200 mL) and to this mixture was added triethylamine (79 mL, 0.57 mol) and Boc20 (68 g, 0.31 mol) at 0 °C. The cooling bath was removed and the reaction mixture was stirred at ambient temperature overnight and then diluted with MTBE (300 mL). The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford (5)-methyl 2- ((tert-butoxycarbonyl)amino)-3-hydroxypropanoate (60 g, 94percent yield) as a colorless oil.
to a solution of L-serine methyl ester hydrochloride (10.00 g, 64.5 mmol) and Boc20 (28.12 g, 129 mmol) in THF (258 ml_) was slowly added Et3N (27 ml_, 194 mmol) at room temperature. The reaction was stirred overnight, then quenched with saturated NaHC03 and brine, concentrated under vacuum and diluted with CH2CI2 and brine. The mixtures were separated and the aqueous layers were extracted with CH2CI2 three times, the combined organic phases were washed with brine, dried andiconcentrated, the residue was purified by silica gel column chromatography which gave the title compound as colourless oil (14.147 g, 86 percent yield).
Synthesis of N-t-butoxycarbonyl-D,L-serine methyl ester (65) , Triethylamine[1.78 ml(12.5 mmol.)] was added, under stirring at room temperatre, to a solution of DL-serine methyl ester hydrochloride[3.89 g(12.5 mmol.)] in methylene chloride(50 ml), and the mixture was stirred for 30 minutes, and there was added di-t-butyl dicarbonate[6.00 g(13.8 mmol.)].
The whole mixture was stirred for 20 hours at room temperature. The reaction mixture was washed with 1N aqueous solution of sodium hydroxide and water, successively, and dried, and then the solvent was distilled off.
The residue was subjected to column chromatography using silica gel, and eluted with hexane-ethyl acetate(2:1), to obtain the desired product (65)[2.80 g(51.1percent)] as a colorless oily substance.
IR(Neat)cm-1: 3370(br), 1740(br), 1700(br).
NMR(90 MHz,CDCl3) δ: 1.45(9H,s), 3.77(3H,s), 3.90(2H,m), 4.35(1H,m), 5.50(1H,br.d,J=7 Hz).

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