N-(Diphenylmethylene)glycine ethyl ester

white to light yellow crystalline powder or

Preparation of benzophenone glycine imine ethyl ester. In a 1 litre glass reactor equipped with a distillation section and a Dean and Stark separator, 182g (1 mole) of benzophenone, 70.1g (0.5 mole) of glycine ethyl ester hydrochloride, 4.75g (0.05 mole) of paratoluenesulfonic acid and 249g of toluene were loaded. The mixture was heated at 110-115°C at atmospheric pressure to give a good reflux in toluene. 97g (1.05 mole) of N, N-diisopropyl N-ethyl amine was added by pump over 4 hours. During the reaction, water was formed and was distilled off as water-toluene azeotrop. Water was decanted in the Dean and Stark seprator and toluene was returned to the reactor. Reaction was pursued for 1 hour after the end of the amine addition and completion of the reaction was monitored by liquid chromatography. When reaction was complete, the reaction mixture was cooled down to 20°C. The mixture was then washed with 335g of water and the 2 liquid phases were separated by decantation. The bottom aqueous phase containing all N, N-diisopropyl N-ethyl amine hydrochloride was kept for treatment by aqueous sodium hydroxide to recover N, N-diisopropyl N-ethyl amine for recycle. The upper toluen phase containing benzophenone glycine imine ethyl ester and the excess benzophenone was concentrated during which operation water was removed as an azeotrope with toluene. The dry solution, of benzophenone glycine imine ethyl ester in toluene was assayed by liquid chromatography : a 91 percent yield of benzophenone glycine imine ethyl ester was obtained with respect to glycine ethyl ester hydrochloride.2.1 Step 3: To a 500 mL three neck RB flask equipped with a distillation and a Dean-Stark separator, benzophenone (20 g, 109.8 mmol), glycine ethyl ester Hydrochloride (15.32 g, 109.8mmol), p-toluenesulfonic acid (0.522 g, 2.745 mmol) and 400 mL of toluene were added. The mixture was heated at 115 C with stirring to get a good reflux in toluene. Finally N, Ndiisopropyl ethyl amine (14.4 mL, 82.35 mmole) was added using a dropping funnel over 45 mm. During the reaction, water was formed which was decanted from the Dean-Stark separator and toluene were returned to the reactor. The reaction was monitored by TLC, and it took about18 h for 50percent completion. The reaction mixture was cooled down to room temperature, and extracted (3 x 100 mL) with ethyl acetate, collected organic layer and washed organic layer once with saturated NaCI solution. The organic layer separated, dried over Na2504, and distilled off the volatiles to get crude material, which was flash chromatographed to get 9.0 g (30percent isolated) ofEthyl-2-(diphenylmethyleneamino) acetate as a white solid, which was confirmedbyH1NMR.Glycine ethyl ester hydrochloride (1.00 g, 7.16 mmol) was dissolved in dry DCM (40 ml). Benzophenone imine (1.20 ml, 7.16 mmol) was added dropwise. The RM was stirred at rt for 18 h. The RM was filtered through Celite, washed with DCM and the filtrate concentrated in vacuo. The resulting oil was triturated with hexane to give the desired product as a white solid.Y = 97 percent MS ESGeneral Procedure A; Preparation of Amino Ester Ketimine from Amino Ester Hydrochloride; Referring to FIG. 6 in the attached drawings, glycine ethyl ester hydrochloride 14b (2.015 g, 14.4 mmol) was suspended in 25 mL dry DCM (dichloromethane) and benzophenone imine (2.42 mL, 14.4 mmol) was added and stirred at room temperature for 8-16 hr. The reaction mixture was filtered, washed with 5 mL DCM and the organic solution was washed 1.x. with HTetrahydropyrrole 0.85 g (12 mmol), Molecular sieve 100g, Glycine ethyl ester 10.3g (100mmol)And benzophenone 27.3g (150mmol)Added to the reaction vessel, 200ml N, N-dimethylformamide as the reaction solvent, Raise the temperature to 50°C for 2 to 3 hours.The reaction solution was cooled to room temperature, poured into water, extracted with dichloromethane, and concentrated under reduced pressure.Column chromatography afforded glycine ethyl benzophenone imine 26.2g, a yield of 98.1percent, purity 99.25percent.139.6 g of glycine ethyl ester, 400 g of benzophenone, 9.5 g of p-toluenesulfonic acid (PTS) and 400 ml of toluene were added to the reaction flask, and the temperature was raised to reflux, and diisopropylethylamine was slowly added to the reaction system. After diisopropylethylamine was added dropwise, the reaction was continued for 2 hours. The reaction solution was cooled to room temperature, 300 ml of water and 200 ml of toluene were added, stirred, and the layers were allowed to stand. The toluene layer was washed once with brine. The toluene layer was concentrated to dryness to give 490 g of liquid benzophenone glycine imide ethyl ester in 93percent yield.

Molecular Weight:267.32
XLogP3:3.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:267.125928785
Monoisotopic Mass:267.125928785
Topological Polar Surface Area:38.7
Heavy Atom Count:20
Complexity:306
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes