CAS: 181289-34-9; (S)-3-(Carbamoylmethyl)-5-Methylhexanoic Acid

该化合物是一种手性碳本体酸衍生物,在三处有一个氨-氧乙基替代物,在六乙酸脊柱的五处有一个甲基组别.(3S)-立体化学确保了对应纯度,使其对不对称合成和药物应用具有价值.碳箱基和氨化物功能组的存在增强了其作为多功能中间体在浸泡改变或生物活性分子开发中的效用.它定义的立体中心和结构模型有助于精确的分子相互作用,特别是在药物设计和酶学研究中.该化合物的稳定性和功能组群的兼容性进一步支持其在受控有机转化中的使用.

英文名称(S)-3-(Carbamoylmethyl)-5-Methylhexanoic Acid
中文名称(+)-5-氨基-3-(S)-异丁基戊二酸
其它别名Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (S)- (9CI)
CAS编号181289-34-9
MFCD编号:MFCD17676409
FDA UNII编号:ZG9DTT4Q9Q
分子式:C9H17NO3分子量:187.24
产品CID: 934548
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: NPDKTSLVWGFPQG-ZETCQYMHSA-N
1S/C9H17NO3/c1-6(2)3-7(4-8(10)11)5-9(12)13/h6-7H,3-5H2,1-2H3,(H2,10,11)(H,12,13)/t7-/m0/s1
计算化学: 氢键受体数3.0氢键供体数2.0可旋转键数6.0

MSDS等安全信息

警示词warning
危险描述H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body
防范说明P264+P280+P305+P351+P338+P337+P313
安全声明H303+H313+H333

上下游产品

(+/-)3(carbamoylmethyl)5methylhexanoic acid (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid 20H30O3SC20H30O3S5-methyl-3-carboxymethylhexanoic acid pregabilin (+/-)3(carbamoylmethyl)5methylhexanoic acid (3R)-3-(carbamoylmethyl)-5-methylhexanoic acid

合成工艺路线路线简述

合成目标产物 Hexanoicacid, 3-(2-Amino-2-Oxoethyl)-5-Methyl-, (3S)- 主要起始原料 (3S)-3-(2-Methoxy-2-Oxoethyl)-5-Methylhexanoic Acid
(文献来源)合成步骤主要原料 (3S)-3-(2-Methoxy-2-Oxoethyl)-5-Methylhexanoic Acid

📜3-(氨甲酰甲基)-5-甲基己酸置于(S)-(-)-α-甲基苄胺,盐酸体系中,用乙醇,氯仿,水用作溶剂,化学反应 1.5H,以16 G的收率获得(+)-5-氨基-3-(S)-异丁基戊二酸
参考文献:抗惊厥药普瑞巴林杂质的合成与表征
标题:抗惊厥药普瑞巴林杂质的合成与表征
摘要:在普瑞巴林 1(一种已知的抗惊厥药物)的工艺开发过程中,Lcms 在最终原料中发现了 0.01% 至 0.15% 的六种潜在杂质.随后合成了所有六种杂质,并通过 Ir,Ms 和 NMR 光谱数据对其进行了表征.六种相关物质中有四种被称为 4-Isobutylpyrrolidin-2-One 6,3-Isobutylglutaric Acid 2,(R)-(-)-3-Carbamoylmethyl-5-Methylhexanoic Acid 5 和 (R)-(-)-3-氨基甲基-5-甲基己酸8,(S)-3-氨基甲基-5-甲基己酸异丁酯9和(S)-3-氨基甲基-5-甲基己酸异丙酯10是首次报道的新化合物在我们的过程中.目前的工作描述了这些杂质的形成,合成和表征.
Doi:10.3998/ark.5550190.0011.A22

海关参考信息

2905121000-正丙醇
2905130000-正丁醇
2912110000-甲醛
2912120000-乙醛
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-8476441-B2
优先权日:2009-01-29
标题 :Intermediates in the enantioselective synthesis of 3-(aminomethyl)-5-methyl-hexanoic acid
发明人：CONNON STEPHEN JOSEPH; PESCHIULLI ALDO; MARKEY LYN
权利人:CONNON STEPHEN JOSEPH; PESCHIULLI ALDO; MARKEY LYN; TRINITY COLLEGE DUBLIN
摘要:(S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid or (S)-pregabalin is an anticonvulsive drug. In addition to its use as an anticonvulsive agent, pregabalin has also been indicated as a medicament in the treatment of anxiety, neuropathic pain and pain in patients with fibromyalgia. Provided herein are thioester intermediates in the synthesis of and processes for the synthesis of 3-(aminomethyl)-5-methyl-hexanoic acid in the (R) or (S) configuration.

专利号:WO-2023088077-A1
优先权日:2021-11-21
标题 :Biocatalysts and methods for the synthesis of pregabalin intermediates

专利号:US-2025043323-A1
优先权日:2021-11-21
标题 :Biocatalysts and methods for the synthesis of pregabalin intermediates

专利号:US-8563775-B2
优先权日:2006-07-04
标题:Process for the preparation of (R)-(âˆ’)-3-(carbamoylmethyl)-5-methylhexanoic acid and of pregabalin and synthesis intermediates
发明人：SALVI ANNIBALE; NARDI ANTONIO; DE ANGELIS BRUNO
权利人:SALVI ANNIBALE; NARDI ANTONIO; DE ANGELIS BRUNO; LABORATORIO CHIMICO INT SPA
摘要:This invention relates to the preparation of (R)-(âˆ’)-3-(carbamoylmethyl)-5-methylhexanoic acid, in particular, the resolution of the acid racemate by means of salification with optically active amines and subsequent acidification to give the (R) enantiomer of the acid; this invention also concerns the salt intermediates formed with said amines and the conversion of said (R)-(âˆ’)-3-(carbamoylmethyl)-5-methylhexanoic acid into biologically active molecules such as pregabalin.

专利号:US-2012046468-A1
优先权日:2009-01-29
标题 :Intermediates in the enantioselective synthesis of 3-(aminomethyl)-5-methyl-hexanoic acid

专利号:CN-117425732-A
优先权日:2021-11-21
标题 :Biocatalysts and methods for the synthesis of pregabalin intermediates