CAS: 71989-33-8; Fmoc-Ser(Tbu)-Oh

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Fmoc-L-丝氨酸甲酯置于aluminum (Iii) Chloride,高氯酸体系中,用 乙酸乙酯 作为反应溶剂,化学反应 1.0H,反应生成 Fmoc-O-叔丁基-L-丝氨酸
参考文献:一种制备fmoc-Ser(Tbu)-Oh的方法
标题:一种制备fmoc-Ser(Tbu)-Oh的方法
摘要:本发明涉及一种制备fmoc‑ser(Tbu)‑oh的方法,属于医药中间体化工技术领域.本发明解决的技术问题是提供制备fmoc‑ser(Tbu)‑oh的方法.该方法包括如下步骤:A,Ser‑or.hcl与fmoc‑osu反应,得到fmoc‑ser‑or固体;b,Fmoc‑ser‑or固体,醋酸叔丁酯,高氯酸和叔丁醇混合,15~40oc反应后,调ph=5~6,析出固体,过滤,洗涤,干燥,得到fmoc‑ser(Tbu)-or固体;c,水解:Fmoc‑ser(Tbu)-or固体水解得到fmoc‑ser(Tbu)‑oh产品.本发明方法,在先引入fmoc基团,可以减少脱除皂化过程中的消旋风险,在引入叔丁基时采用醋酸叔丁酯,高氯酸,叔丁醇和fmoc‑ser‑or中的羟基进行反应,操作简单可控,安全性好,所得产品手性纯度高,成本低,能有效缩短生产步骤,提高生产效率及产率,适应于现代工业生产.

专利信息

专利号:US-8828938-B2
优先权日:2009-04-24
标 题:Method for the manufacture of degarelix
发明人：ZHANG HAIXIANG; FOMSGAARD JENS; STAERKAER GUNNAR
权利人:POLYPEPTIDE LABORATORIES AS
摘要:In a step-wise synthesis of degarelix comprising 0.3% by weight or less of 4-([2-(5-hydantoyl)]acetylamino)-phenylalanine analog on (solid support)-NH 2 a step comprises providing a solution of an amino acid or peptide of which the α-amino group is protected by Fmoc; contacting the support with the solution in the presence of reagent for forming a peptide bond between a carboxyl group of the amino acid or peptide and (solid support)-NH 2 ; removing Fmoc by contacting the support with an organic base, in particular piperidine, in an organic solvent. Also disclosed is degarelix of high purity prepared by the method of the invention and the use of Fmoc in the synthesis of degarelix.

专利号:US-12098218-B2
优先权日:2015-12-17
标题 :Process for the manufacture of degarelix and its intermediates
发明人：RICCI ANTONIO; ZANON JACOPO; CABRI WALTER; GURYANOV IVAN; ORLANDIN ANDREA; BIONDI BARBARA; FORMAGGIO FERNANDO; VISENTINI DARIO
权利人:FRESENIUS KABI IPSUM S R L
摘要:The present invention provides a manufacturing process for preparing a peptide, preferably a decapeptide, such as degarelix, by incorporating p-nitro-phenylalanin in the amino acid sequence preferably during stepwise solid phase synthesis, and converting these into the required amino acids Aph(Hor) and/or D-Aph(Cbm), preferably while attached to a solid phase. The invention further provides intermediates useful in the manufacturing process.

专利号:US-2024076311-A1
优先权日:2020-12-28
标 题:Method for synthesizing peptide thioesters and head-to-tail amide cyclic peptide thereof
发明人：CHEN ZHILI; TAO TONGQIANG; TAN BAOFENG; ZHANG XIN
权利人:JIANGSU GENSCRIPT BIOTECH CO LTD
摘要:A method for synthesizing peptide thioesters and a head-to-tail amide cyclic peptide thereof, which belongs to the technical field of chemical pharmaceuticals and fine chemical preparation. The method comprises the following steps: (1) using resin A as a carrier and using a solid-phase synthesis strategy to obtain a resin peptide; (2) cutting the resin to obtain a fully protected peptide; (3) performing an esterification reaction with p-chlorophenyl thiophenol in a TCFH/alkali condensation system to generate p-chlorophenyl thioester; (4) removing the protecting group to obtain a peptide thioester; and (5) further cyclizing to obtain a head-to-tail cyclic peptide. The preparation of the thioester peptide and the head-to-tail amide cyclic peptide provides a simple technical route with wide universality and a high yield, and has a wide range of applications in the technology of chemical pharmaceuticals and fine chemical preparation.