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2.75 g (23.5 mmol) of <strong>[3154-54-9]N-formyl glycine methyl ester</strong> is dissolved in 100 mL of re-distilled anhydrous dichloromethane (DCM), and then triethylamine 8.1 is added mL (58.7 mmol), and the reaction mixture was cooled in an ice bath with stirring for 15 min. After cooling was completed, 2.2 mL (23.5 mmol) of phosphorus oxychloride was slowly added dropwise to the inverted system, and then the reaction was continued in an ice bath with stirring for 1 h. The solution was then warmed to room temperature, and a saturated Na2CO3 solution was slowly added until the pH showed alkaline. Stirring was continued until the aqueous and organic phases were fully separated, the organic layer was separated from the separatory funnel, and the aqueous layer was extracted with DCM (30 mL x 3). The organic layers were combined, washed three times with saturated brine, and the organic phase was dried over anhydrous MgSO4, filtered and washed. The filtrates were combined and spin-dried to obtain the crude alpha-isocyanoacetate. After drying, 1.51 g of a dark brown liquid with a strong pungent odor was obtained with a yield of 65.0%.
EXAMPLE III Preparation of N-(diethylphosphonomethyl), N-(formyl)glycinemethyl ester To 0.32 g (0.0132 mole) of dry sodium hydride taken in 10 ml of tetrahydrofuran was added 2.35 g of diethyl N-(formyl)aminomethyl phosphonate in 10 ml tetrahydrofuran and then stirred at room temperature under N2 for 30 minutes. To the clear solution obtained was added 1.3 g (0.012 mole) of methylchloroacetate and stirred at ambient temperature for 12 hours. The product obtained was a cloudy yellow solution which was filtered through celite, washed with tetrahydrofuran and then stripped at 40 C. with high vacuum. The resulting product was 2.34 g of a cloudy yellow solution. Structure was confirmed as N-(diethylphosphonomethyl)-N-(formyl)glycinemethyl ester by GC and MS. (GC is gas chromatography; MS is mass spectroscopy).
17
[ 3154-54-9 ]
[ 105-34-0 ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; trichlorophosphate; In dichloromethane; at 0℃; for 1h;
Step 1[00233] To a solution of <strong>[3154-54-9]N-formylglycine methyl ester</strong> (LXXII) (27.5 g, 235 mmol) in DCM was added TEA (81.3 mL, 587 mmol). The reaction mixture was cooled to 0C before adding POCI3 (21.6 mL, 235 mmol) dropwise. The reaction was stirred for 1 h. The solution was warmed to room temperature and saturated aqueous Na2S03 was added dropwise. After 30 min., the phases were separated and the aqueous layer was washed with DCM. The combined organic layers were washed with brine, dried over MgS04 and concentrated under vacuum to give crude methyl 2-isocyanoacetate (LXXIII) as a dark brown oil (30 g). The crude product was used for the next step without purification
weigh 3.56 g (0.4 mol) of glycine methyl ester, 10 mL of methyl formate, and 5 mL of triethylamine into a reaction flask, and stir at room temperature for 3 days, then place the reaction flask Allow to stand for 30 min at 0C to precipitate solids and remove solid impurities by filtration; spin-dry the liquid under reduced pressure to obtain a colorless oily substance. TLC test shows that the purity is qualified and does not require further separation and purification; put the oil in a vacuum drying box to dry There was obtained 2.95 g of a colorless liquid with a yield of 78.0%.
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