(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol | 160233-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol
• 英文别名: (2R,3S)-3-amino-1-chloro-4-phenylbutan-2-ol
• CAS: 160233-25-0
• 化学式: C₁₀H₁₄ClNO
• 分子量: 199.68
• InChiKey: YXWOYBQZWSLSMU-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzotriazol-1-yl (2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoate 、 (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol 在 dipotassium hydrogenphosphate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 methyl [(2S)-1-{[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]amino}-3,3-dimethyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF 3,4-EPOXY-2-AMINO-1-SUBSTITUTED BUTANE DERIVATIVES AND INTERMEDIATE COMPOUNDS THEREOF
  [FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE BUTANE 3,4-ÉPOXY-2-AMINO-1-SUBSTITUÉS ET LEURS COMPOSÉS INTERMÉDIAIRES

  摘要：

  本发明涉及一种制备一般式I所代表的threo-3,4-环氧-2-氨基-1-取代丁烷衍生物的方法，包括将一般式III化合物或其盐与一般式IV酸的活性酯反应，并用碱处理其产物。在公式I和IV中与基团R3键合的碳原子处于(R)-、(S)-或(R,S)-构型。公式I和III的化合物，特别是它们的(2S,3R)构型，可用作atazanavir硫酸盐的中间体。

  公开号：

  WO2009136365A1
• 作为产物：
  描述：

  1,1-dimethylethyl[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate 、 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane 在 (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol 、 methyl [(2S)-1-{[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]amino}-3,3-dimethyl-1-oxobutan-2-yl]carbamate 作用下， 以without isolating (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol (Formula III), methyl[(2S)-1-{[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]amino}-3,3-dimethyl-1-oxobutan-2-yl]carbamate (Formula IV) and/or methyl[(2S)-3,3-dimethyl-1-({ (1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate (Formula V) intermediate compounds的产率得到(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol
  参考文献：
  名称：

  US20140343290A1

  摘要：

  公开号：
• 作为试剂：
  描述：

  1,1-dimethylethyl[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate 、 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane 在 (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol 、 methyl [(2S)-1-{[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]amino}-3,3-dimethyl-1-oxobutan-2-yl]carbamate 作用下， 以without isolating (2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol (Formula III), methyl[(2S)-1-{[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]amino}-3,3-dimethyl-1-oxobutan-2-yl]carbamate (Formula IV) and/or methyl[(2S)-3,3-dimethyl-1-({ (1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate (Formula V) intermediate compounds的产率得到(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol
  参考文献：
  名称：

  US20140343290A1

  摘要：

  公开号：

文献信息

• Production method of aminochlorohydrin sulfate
  申请人：Ajinomoto Co., Inc.

  公开号：EP1777213A1

  公开（公告）日：2007-04-25

  Highly pure (2R,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane or (2S,3R)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane may be conveniently produced in high yield by: (a) reacting compound (1) with lithiumchloromethane to give compound (2) and at least a byproduct; (b) dissolving compound (2) and the byproduct in a polar solvent and adding water to the solution to precipitate compound (2) as crystals; (c) reducing the crystals of compound (2) to give compound (3) and at least its diastereomer as an impurity; (d) adding sulfuric acid thereto to give compound (4) and at least its diastereomer as an impurity; and (e) precipitating compound (4) as crystals from a solution containing acetic acid ester or acetic acid ester.

  (2R,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane或(2S,3R)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane可以通过以下步骤方便地高产率地制备：(a)将化合物(1)与氯甲基锂反应，得到化合物(2)和至少一种副产物；(b)将化合物(2)和副产物溶解在极性溶剂中，并向溶液中加入水，使化合物(2)以晶体形式沉淀出来；(c)将化合物(2)的晶体还原，得到化合物(3)和至少其对映异构体作为杂质；(d)加入硫酸至其中，得到化合物(4)和至少其对映异构体作为杂质；(e)从含有乙酸酯或乙酸酯的溶液中沉淀化合物(4)为晶体。
• [EN] PROCESS FOR PREPARATION OF ATAZANAVIR OR ITS BISULFATE SALT<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ATAZANAVIR OU DE SON SEL BISULFATE
  申请人：RANBAXY LAB LTD

  公开号：WO2013014633A1

  公开（公告）日：2013-01-31

  The present invention relates to an improved process for the preparation of atazanavir bisulfate, an inhibitor of retroviral aspartate protease. The process of the present invention comprises conversion of 1,1-dimethylethyl[(2S,3R)-4-chloro-3-hydroxy- -phenylbutan-2-yl]carbamate (Formula II) into 1-[4-(pyridine-2-yl)-phenyl]-4(S)-5 hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert- leucyl)amino-6-phenyl-2-azahexane (Formula VII) without isolating intermediate compounds formed therein, followed by its subsequent conversion to atazanavir or its bisulfate salt.

  本发明涉及一种改进的制备阿扎那韦硫酸盐的方法，阿扎那韦是一种逆转录病毒天冬氨酸蛋白酶抑制剂。本发明的方法包括将1,1-二甲基乙基[(2S,3R)-4-氯-3-羟基苯丁基]氨基甲酸酯（式II）转化为1-[4-(吡啶-2-基)-苯基]-4(S)-5-羟基-2-N-叔丁氧羰基氨基-5(S)-N-(N-甲氧羰基-(L)-叔亮氨酰)氨基-6-苯基-2-氮杂己烷（式VII），而不需要分离其中形成的中间化合物，然后将其进一步转化为阿扎那韦或其硫酸盐。
• [EN] REDUCTION OF ALDEHYDES AND KETONES TO ALCOHOLS<br/>[FR] RÉDUCTION D'ALDÉHYDES ET DE CÉTONES EN ALCOOLS
  申请人：AMERICAN PACIFIC CORP

  公开号：WO2011060302A1

  公开（公告）日：2011-05-19

  The embodiments described herein provide a reduction of an aldehyde or a ketone, such as a Meerwein-Ponnorf-Verley (MPV) reaction of an aldehyde or ketone. In some embodiments, the reaction occurs in the presence of A1[OC(CH3)3]. In some embodiments, the reaction occurs in the presence of an aprotic solvent. In some embodiments, the aldehyde or ketone is an amino aldehyde or an amino ketone wherein the amine is group is protected such that the nitrogen of the amine has no proton. Other embodiments related to compositions and compounds related to the reduction reaction, or to the preparation or use of the aldehyde, the ketone, or the resulting alcohol.

  本文所述实施例提供了醛或酮的还原，例如醛或酮的Meerwein-Ponnorf-Verley(MPV)反应。在某些实施例中，反应发生在A1 [OC(CH3)3]的存在下。在某些实施例中，反应发生在无极溶剂的存在下。在某些实施例中，醛或酮是氨基醛或氨基酮，其中氨基团被保护，使得氨基的氮没有质子。其他实施例涉及与还原反应相关的组合物和化合物，或与醛、酮或所得醇的制备或使用相关的实施例。
• PROCESS FOR THE PREPARATION OF 3,4-EPOXY-2-AMINO-1-SUBSTITUTED BUTANE DERIVATIVES AND INTERMEDIATE COMPOUNDS THEREOF
  申请人：Singh Rakesh

  公开号：US20110178305A1

  公开（公告）日：2011-07-21

  The present invention relates to a process for the preparation of threo-3,4-epoxy-2-amino-1-substituted butane derivatives represented by general Formula I which comprises reacting compound of Formula III or salt thereof with an active ester of acid of Formula IV and treating the product thereof with base. The carbon atom bonded to the radical R 3 in Formula I and IV is in the (R)-, (S)- or (R,S)-configuration. The compounds of Formula I and III, particularly in their (2S,3R) configuration are useful intermediates for the preparation of atazanavir bisulfate.

  本发明涉及一种制备一般式I所表示的threo-3,4-环氧-2-氨基-1-取代丁烷衍生物的过程，该过程包括将一般式III化合物或其盐与一般式IV的酸的活性酯反应，然后用碱处理其产物。在公式I和IV中与基团R3键合的碳原子处于(R)-、(S)-或(R,S)-构型。一般式I和III的化合物，特别是它们的(2S,3R)构型，是制备阿扎那韦双硫酸盐的有用中间体。
• KETOREDUCTASE-MEDIATED STEREOSELECTIVE ROUTE TO ALPHA CHLOROALCOHOLS
  申请人：Bong Yong Koy

  公开号：US20120190086A1

  公开（公告）日：2012-07-26

  The present disclosure relates to engineered ketoreductase polypeptides and uses thereof for the preparation of α chloroalcohols from α chloroketones. Also provided are polynucleotides encoding the engineered ketoreductase polypeptides and host cells capable of expressing the engineered ketoreductase polypeptides.

  本公开涉及工程化的酮还原酶多肽及其在制备α-氯代醇中的应用。还提供了编码工程酮还原酶多肽的多核苷酸和能够表达工程酮还原酶多肽的宿主细胞。