N-acetyl-O-methyl-L-serine | 65022-11-9

• 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
• 英文名称: N-acetyl-O-methyl-L-serine
• 英文别名: N-acetyl-O-methyl-D,L-serine；N-Acetyl-O-methylserine；(2S)-2-acetamido-3-methoxypropanoic acid
• CAS: 65022-11-9
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: SDNGNSKFWTZCJG-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 Rh on carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (R)-2-N-acetamido-3-methoxypropionic acid 、 N-acetyl-O-methyl-L-serine 、 N-乙酰-DL-丙氨酸
  参考文献：
  名称：

  Ramer, Shawn E.; Moore, Richard N.; Vederas, John C., Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713

  摘要：

  DOI：

文献信息

• [EN] NOVEL PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES<br/>[FR] PROCÉDÉ INÉDIT DE FABRICATION DE DÉRIVÉS D'ACIDES AMINÉS
  申请人：UCB PHARMA SA

  公开号：WO2010052011A1

  公开（公告）日：2010-05-14

  The present patent application relates to an alternative process for the preparation of amino derivatives. In particular, the present application relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide, which is useful as an anticonvulsive drug. In a particular aspect, the present invention relates to a process of manufacture of optically enriched (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (I) comprising resolution of 2-acetamido-N-benzyl-3-methoxypropion-amide (II).

  本专利申请涉及一种用于制备氨基衍生物的替代工艺。具体来说，本申请涉及一种改进的工艺，用于制造拉科萨胺（LCM），即（R）-2-乙酰氨基-N-苄基-3-甲氧基丙酰胺，该物质可用作抗惊厥药物。在一个特定方面，本发明涉及一种制造光学富集的（R）-2-乙酰氨基-N-苄基-3-甲氧基丙酰胺（I）的工艺，包括对2-乙酰氨基-N-苄基-3-甲氧基丙酰胺（II）进行分离。
• Process for the preparation of Lacosamide including resolution of O-methyl-DL-serine
  申请人：UCB Pharma GmbH

  公开号：EP2487152A1

  公开（公告）日：2012-08-15

  The present invention provides a process for the preparation of lacosamide in substantially optically pure form, which in one aspect comprises the following steps: (i) resolution of O-methyl-D,L-serine to provide O-methyl-D-serine in substantially optically pure form; (ii) acetylation of O-methyl-D-serine thereby obtained to provide the N-acetyl derivative thereof in substantially optically pure form; (iii) activating the carboxy group of the compound thereby obtained; and (iv) reacting the compound thereby obtained with benzylamine.

  本发明提供了一种制备几乎光学纯度的拉科萨米德的方法，其中一方面包括以下步骤：(i) 分离O-甲基-D，L-丝氨酸以提供几乎光学纯度的O-甲基-D-丝氨酸；(ii) 乙酰化由此得到的O-甲基-D-丝氨酸，以提供几乎光学纯度的其N-乙酰衍生物；(iii) 激活所得化合物的羧基；和 (iv) 用苄胺与所得化合物反应。
• [EN] PROCESS FOR PREPARING LACOSAMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN LACOSAMIDE
  申请人：UCB PHARMA GMBH

  公开号：WO2012065891A1

  公开（公告）日：2012-05-24

  The present invention provides a process for the preparation of lacosamide in substantially optically pure form, which in one aspect comprises the following steps: (i) resolution of O-methyl-D,L-serine to provide O-methyl-D-serine in substantially optically pure form; (ii) acetylation of O-methyl-D-serine thereby obtained to provide the N-acetyl 10 derivative thereof in substantially optically pure form; (iii) activating the carboxy group of the compound thereby obtained; and (iv) reacting the compound thereby obtained with benzylamine.

  本发明提供一种制备几乎光学纯度的拉科萨米德的方法，其中一方面包括以下步骤：(i)分离O-甲基-D，L-丝氨酸以提供几乎光学纯度的O-甲基-D-丝氨酸；(ii)乙酰化因此获得的O-甲基-D-丝氨酸，以提供几乎光学纯度的N-乙酰基10衍生物；(iii)激活所获得化合物的羧基；以及(iv)将所获得的化合物与苄基胺反应。
• [EN] ENZYMATIC RESOLUTION OF RACEMIC (2R,S)-2-(ACETYLAMINO)-3-METHOXY-N-(PHENYLMETHYL)PROPANAMIDE<br/>[FR] RÉSOLUTION ENZYMATIQUE DU (2R,S)-2-(ACÉTYLAMINO)-3-MÉTHOXY-N-(PHÉNYLMÉTHYLE) PROPANAMIDE RACÉMIQUE
  申请人：MEDICHEM SA

  公开号：WO2011158194A1

  公开（公告）日：2011-12-22

  The present invention is concerned with a process of preparing (R)-lacosamide. The process comprises providing an (R,S)-lacosamide precursor and contacting the same with at least an enzyme in the presence of a solvent. The enzyme either stereoselectively hydrolyzes or acetylates an (R)- or (S)-enantiomer of the (R,S)-lacosamide precursor. The process further comprises where appropriate also concurrently, or successively, employing one or more reagents capable of converting the hydrolysed or acetylated (R)- or (S)-enantiomer to (R)- lacosamide.

  本发明涉及一种制备(R)-拉科莎胺的方法。该方法包括提供(R,S)-拉科莎胺前体，并在溶剂存在下与至少一种酶接触。酶可以立体选择性地水解或乙酰化(R)-或(S)-对映体的(R,S)-拉科莎胺前体。该方法还包括，在适当的情况下同时或依次使用能够将水解或乙酰化的(R)-或(S)-对映体转化为(R)-拉科莎胺的一种或多种试剂。
• Novel Process for the Preparation of Amino Acid Derivatives
  申请人：Bouvy Didier

  公开号：US20110263899A1

  公开（公告）日：2011-10-27

  The present patent application relates to an alternative process for the preparation of amino derivatives. In particular, the present application relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide, which is useful as an anticonvulsive drug. In a particular aspect, the present invention relates to a process of manufacture of optically enriched (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (I) comprising resolution of 2-acetamido-N-benzyl-3-methoxypropion-amide (II).

  本专利申请涉及一种制备氨基衍生物的替代工艺。特别地，本申请涉及一种改进的制备Lacosamide（LCM），即(R)-2-乙酰氨基-N-苄基-3-甲氧基丙酰胺，该药物可用作抗癫痫药物的工艺。在特定方面，本发明涉及一种制备光学富集的(R)-2-乙酰氨基-N-苄基-3-甲氧基丙酰胺（I）的工艺，包括分离2-乙酰氨基-N-苄基-3-甲氧基丙酰胺（II）。