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Scalable Synthesis of 8-Amino-3-hydroxy-6H-benzo[c]chromen-6-one: Key Intermediate for SEGRA via the Hurtley Reaction
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2014-12-24 00:00:00 , DOI: 10.1021/op500334b Kazuhiro Kudo 1, 2 , Noriyoshi Yamamoto 1
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2014-12-24 00:00:00 , DOI: 10.1021/op500334b Kazuhiro Kudo 1, 2 , Noriyoshi Yamamoto 1
Affiliation
A practical and scalable process for the preparation of 8-amino-3-hydroxy-6H-benzo[c]chromen-6-one in multihundred kilogram amounts has been developed. The key features of this synthesis are the application of the Hurtley reaction with a copper and base combination and the development of a purification process. The new synthesis improved the total yield from 49.0% to 59.5% and reduced the number of steps from three to two. Compared with the conventional medicinal route, manufacturing costs were reduced significantly by the use of inexpensive, easy to procure materials.
中文翻译:
可伸缩合成8-氨基-3-羟基-6 H-苯并[ c ]铬6-1-酮:通过赫特利反应制备SEGRA的关键中间体
已经开发了一种实用且可扩展的方法,用于制备数百公斤量的8-氨基-3-羟基-6 H-苯并[ c ] chromen-6-one。该合成的关键特征是应用赫特利反应与铜和碱的结合以及纯化工艺的发展。新的合成方法将总收率从49.0%提高到了59.5%,并将步数从3个减少到2个。与传统的药物途径相比,通过使用廉价,易于采购的材料,大大降低了制造成本。
更新日期:2014-12-24
中文翻译:
可伸缩合成8-氨基-3-羟基-6 H-苯并[ c ]铬6-1-酮:通过赫特利反应制备SEGRA的关键中间体
已经开发了一种实用且可扩展的方法,用于制备数百公斤量的8-氨基-3-羟基-6 H-苯并[ c ] chromen-6-one。该合成的关键特征是应用赫特利反应与铜和碱的结合以及纯化工艺的发展。新的合成方法将总收率从49.0%提高到了59.5%,并将步数从3个减少到2个。与传统的药物途径相比,通过使用廉价,易于采购的材料,大大降低了制造成本。