Glycine, N-[(2,4-dimethoxyphenyl)methyl]- synthesis
- Product Name:Glycine, N-[(2,4-dimethoxyphenyl)methyl]-
- CAS Number:20839-79-6
- Molecular formula:C11H15NO4
- Molecular Weight:225.24
95218-34-1
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Yield:20839-79-6 100%
Reaction Conditions:
with water;sodium hydroxide in methanol at 20; for 2 h;
Steps:
104
Ethyl bromoacetate (Scheme 28) (10.0 gm, 59.87 mmol) solution in 20.0 mL of anhydrous THF was added dropwise to a solution of (2,4-dimethoxybenzyl)amine (10.0gm, 59.81 mmol) and triethyl amine (6.06 gm, 59.87 mmol) in anhydrous THF (20.0 mL) at 0 °C under nitrogen atmosphere. The reaction mixture was warmed to room temperature and stirred overnight. Brine was added 100 mL, and the reaction mixture was extracted with ethyl acetate (2 x 100 mL). Combined extracts were dried over anhydrous MgSO4 and concentrated under reduced pressure. The purification wasperformed using combiFlash chromatography, Gradient: 20:80 to 50:50 v/v Ethylacetate:Hexane. 7.6 gm (yield 50.2 %) of the alkylation product was obtained as a colorless liquid. m/z calculated for C13H19N04 [M+H]: 254; Obtained: 254.1. The ester (7.5 gm, 29.6 mmol) was dissolved in 40.0 mL of methanol. The reaction mixture was cooled and 2N aq. NaOH (88.82 mmol, 44.0 mL) solution was addeddropwise. The reaction mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was diluted with 75.0 mL of water, cooled in ice bath and neutralized down to 5.0 to 4.5 pH using 2N aq. HC1. The excess water was concentrated under reduced pressure and air streamed to obtain white solid powder. The solid was dissolved in 85:15 v/v, DCM:MeOH (100.0 mL) and filtered, the filtrate was evaporated to obtain7.1 gm of carboxylic acid as a white powder (Hygroscopic). m/z calculated for C11H15N04 [M+Na]: 248; Obtained: 248.1.
References:
WO2016/205739,2016,A1 Location in patent:Paragraph 0447
20781-20-8
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