N2-羧基-O-甲基-N2-(2-甲基-2-丙基)丝氨酰胺 | 161561-84-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N2-羧基-O-甲基-N2-(2-甲基-2-丙基)丝氨酰胺
• 英文名称: tert-butyl (S)-N-(1-carbamoyl-2-methoxyethyl)carbamate
• 英文别名: N-Boc-O-methyl-L-serinamide；N²-Boc-O-methyl-L-serinamide；((S)-1-carbamoyl-2-methoxyethyl)carbamic acid tert-butyl ester；tert-butyl N-[(2S)-1-amino-3-methoxy-1-oxopropan-2-yl]carbamate
• CAS: 161561-84-8
• 化学式: C₉H₁₈N₂O₄
• 分子量: 218.253
• InChiKey: LNBYIYCVIDOMDM-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N2-羧基-O-甲基-N2-(2-甲基-2-丙基)丝氨酰胺 在 劳森试剂 、 三氟乙酸 作用下， 以 乙二醇二甲醚 为溶剂， 生成 ethyl 2-[(1S)-2-methoxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Synthesis of an Enantiomerically Pure Serine-Derived Thiazole

  摘要：

  Previously reported methods for preparing enantiomerically pure thiazoles are inadequate for the synthesis of inherently labile O-alkyl serine-derived thiazoles. The intermediate N-Boc-(O-methylseryl) thiazolines are very susceptible to tautomerization, even under neutral conditions (Scheme 5). Herein, it is demonstrated that the choice of N-protecting group is critical to the preservation of enantiomeric purity. Thus, using an N-trityl protecting group, O-methyl serine was converted to the corresponding N-Boc-(O-methylseryl) thiazole 3 with no appreciable epimerization as indicated by F-19 and H-1 NMR of the corresponding Mosher's amide.

  DOI：

  10.1021/jo961408a
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 N-甲基吗啉 、 sodium hydroxide 、 Proton Sponge 、 氨 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 生成 N2-羧基-O-甲基-N2-(2-甲基-2-丙基)丝氨酰胺
  参考文献：
  名称：

  Synthetic studies towards keramamide F

  摘要：

  This communication describes the synthesis of three fragments of the cytotoxic natural product keramamide F.

  DOI：

  10.1016/0040-4039(94)02213-u

文献信息

• HETEROCYCLIC COMPOUNDS AND METHODS OF USE
  申请人：Heald Robert

  公开号：US20120202785A1

  公开（公告）日：2012-08-09

  Formula I compounds, including stereoisomers, geometric isomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological disorders, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  化学式I类化合物，包括立体异构体、几何异构体、互变异构体、代谢物及其药学上可接受的盐，对抑制PI3K的δ异构体以及治疗由脂质激酶介导的疾病，如炎症、免疫性疾病和癌症，具有用途。公开了利用化合物I类进行体外、体内和体内诊断、预防或治疗哺乳动物细胞中的这类疾病，或相关的病理状况的方法。
• [EN] CYSTEINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE CYSTEINE PROTEASE
  申请人：MEDIVIR AB

  公开号：WO2005066180A1

  公开（公告）日：2005-07-21

  A compound of the formula (II) wherein one of R1 and R2 is halo and the other is H or halo; R3 is C1-C4 straight or branched chain, optionally fluorinated, alkyl; R4 is H; or R3 together with R4 and the adjoining backbone carbon defines: a spiro-C5-C7 cycloalkyl, optionally substituted with 1 to 3 substituents selected from halo, hydroxyl, C1-C4 alkyl or C1-C4 haloalkyl; or optionally bridged with a methylene group; or a C4-C6 saturated heterocycle having a hetero atom selected from O, NRa, S, S(=O)2 ; where Ra is H, C1-C4 alkyl or CH3C(=O); R5 is independently selected from H or methyl; E is -C(=O)-, -S(=O)m-, -NR5S(=O)m-, -NR5C(=O)-, -OC(=O)-, R6 is a stable, optionally substituted, monocyclic or bicyclic, carbocycle or hetorocycle; m is independently 0,1 or 2; are inhibitors of cathepsin K and useful in the treatment or prophylaxis of osteoporosis.

  一个公式为(II)的化合物，其中R1和R2中的一个是卤素，另一个是H或卤素；R3是C1-C4直链或支链，可选择氟代的烷基；R4是H；或者R3与R4和相邻的骨架碳一起定义：一个螺环C5-C7环烷基，可选地用1至3个卤素、羟基、C1-C4烷基或C1-C4卤代烷基中的取代基取代；或者可选地用亚甲基桥接；或者是一个具有O、NRa、S、S(=O)2等异原子的C4-C6饱和杂环；其中Ra是H、C1-C4烷基或CH3C(=O)；R5独立地选择自H或甲基；E是-C(=O)-、-S(=O)m-、-NR5S(=O)m-、-NR5C(=O)-、-OC(=O)-；R6是稳定的、可选择取代的、单环或双环的、碳环或杂环；m独立地为0、1或2；是猫hepsin K的抑制剂，并且在骨质疏松症的治疗或预防中有用。
• Bacterial Preparation of Enantiopure Unactivated Aziridine-2-carboxamides and Their Transformation into Enantiopure Nonnatural Amino Acids and <i>vic</i>-Diamines
  作者：Roberto Morán-Ramallal、Ramón Liz、Vicente Gotor

  DOI：10.1021/ol062895b

  日期：2007.2.1

  by kinetic resolution of their racemates by Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis. Several regio- and enantioselective nucleophilic ring openings of (1R,2S)-1-benzylaziridine-2-carboxamide or its LAH-reduced product led to a series of enantiopure products, such as O-methyl-l-serine and some vicinal diamines.

  [反应：见正文]对映体纯（1R，2S）-1-苄基和1-芳基氮丙啶-2-羧酰胺是通过Rhodococcus rhodochrous IFO 15564催化水解而动态消解外消旋物而获得的。（1R，2S）-1-苄基氮丙啶-2-羧酰胺或其LAH还原产物的几个区域和对映选择性亲核开环产生了一系列对映纯产物，例如O-甲基-1-丝氨酸和一些邻位二胺。
• Heterocyclic compounds and methods of use
  申请人：Heald Robert

  公开号：US08653089B2

  公开（公告）日：2014-02-18

  Formula I compounds, including stereoisomers, geometric isomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological disorders, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  包括立体异构体、几何异构体、互变异构体、代谢物和药学上可接受的盐在内的公式I化合物，可用于抑制PI3K的δ异构体，并用于治疗由脂质激酶介导的疾病，如炎症、免疫性疾病和癌症。本文揭示了使用公式I化合物进行哺乳动物细胞内、原位和体内诊断、预防或治疗此类疾病或相关病理状态的方法。
• WO2007/6714
  申请人：——

  公开号：——

  公开（公告）日：——