N-(tert-Butoxycarbonyl)-2-aminoacetonitrile synthesis
- Product Name:N-(tert-Butoxycarbonyl)-2-aminoacetonitrile
- CAS Number:85363-04-8
- Molecular formula:C7H12N2O2
- Molecular Weight:156.18
24424-99-5
151-63-3
85363-04-8
The general procedure for the synthesis of 2-(Boc-amino)acetonitrile from di-tert-butyl dicarbonate and aminoacetonitrile sulfate was as follows: first, 3 mmol of aminoacetonitrile sulfate was dissolved in 50 mL of anhydrous methanol at room temperature and protected by nitrogen. Subsequently, 770 mg (4.5 mmol) of L-cysteine methyl ester hydrochloride and 0.63 mL (4.5 mmol) of triethylamine were added to this solution. The reaction mixture was stirred at room temperature for 3 hours, after which the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and washed sequentially with saturated sodium bicarbonate solution and brine. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated, and finally purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 5:1) to afford a methyl ester derivative of the target product 2-(Boc-amino)acetonitrile. Next, 0.9 mL (0.9 mmol) of a 1N lithium hydroxide solution was added to 1.0 mmol of a 5 mL methanol solution of the above methyl ester derivative at 0 °C. The suspension was stirred at room temperature for 1 h. Upon completion of the reaction, it was diluted with 20 mL of acetone to promote precipitation of the product. The white solid was collected by filtration and dried to give purified 2-(Boc-amino)acetonitrile.
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Yield: 97.1%
Reaction Conditions:
with triethylamine in dichloromethane;water at 20; for 15 h;Cooling with ice;
Steps:
2 Example 2
Add the raw materials aminoacetonitrile hydrochloride (65g, 0.70mol), dichloromethane (650mL) to the reaction flask, stir, add triethylamine (213.27g, 2.1mol, 3eq), cool down in an ice water bath,Add Boc anhydride (229.9, 1.1 mol, 1.5 eq) dropwise, add water (650 mL), separate and wash with water after stirring at room temperature for 15 hours. After drying the organic phase with anhydrous sodium sulfate, filter and concentrate to obtain compound B2 ( 106.5g, 97.1%)
References:
Zhejiang Jingxin Pharmaceutical Co., Ltd.;Shanghai Jingxin Bio-pharmaceutical Co., Ltd.;Guo Sigen;Wu Maojiang;Xu Miaohuan;Xu Hui;Song Liqiang;Li Fengjie;Liu Yunlong CN111620834, 2020, A Location in patent:Paragraph 0052-0056
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85363-04-8
108 suppliers
$6.00/250mg