Related Products of 1000342-11-9, The chemical industry reduces the impact on the environment during synthesis 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, I believe this compound will play a more active role in future production and life.
Step 1 : Synthesis of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl) amino)cyclohexyl)-amino)-2-methylbenzoate: [0671] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (860 g, 3.53 mol) and tert-butyl (4-oxocyclohexyl)carbamate (904.6 g, 4.24 mol) in dichloroethane (1 L), acetic acid (1274 g, 21.23 mol) was added and reaction was stirred at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2250 g, 10.61 mol) was added at 0 C and reaction was stirred at room temperature for 16 hours. On completion (monitored by TLC), reaction was quenched with aqueous sodium bicarbonate, the organic layer was separated and the aqueous layer was extracted with dichloromethane (1.5 L X 3). The combined organic layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography (100-200 mesh size) eluting with 2, 4, 6 & 8% ethyl acetate in hexane to remove maximum cis isomer. This afforded 945 g of mixture of cis and trans isomers (40:60 by HPLC). The trans isomer was purified by repetitive recrystazlisation with ethyl acetate: hexane (1 :2) to afford 480 g of pure trans isomer as white solid with 99% purity.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 3-amino-5-bromo-2-methylbenzoate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10049; (2015); A1;,
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