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Chiral phosphoramides, chiral N-phosphonimines and methods for forming the same

A phosphorimide and phosphoramide technology, applied in the field of design and synthesis of novel chiral imine reagents, can solve the problems of expensive raw materials, odorous disulfides, harmful substances, etc.

Inactive Publication Date: 2010-08-11
NOWA PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the preparation of N-sulfimides requires the use of expensive raw materials or disulfides which are very harmful to the environment (toxic and odorous)

Method used

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  • Chiral phosphoramides, chiral N-phosphonimines and methods for forming the same
  • Chiral phosphoramides, chiral N-phosphonimines and methods for forming the same
  • Chiral phosphoramides, chiral N-phosphonimines and methods for forming the same

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Embodiment

[0053] Synthesis of Chiral Phosphoramides Linked to Free Amino Groups

[0054] There are four steps in the synthesis of the chiral phosphoramide, and the intermediate products in these steps can be directly subjected to the next reaction without purification. Similar to the steps of the synthesis of N-alkyl phosphoramides, protected 1,2-diamines or amino alcohols can be used as raw materials for the preparation of the chiral phosphoramides (S.E.Denmark, Nature, 2006,443,40-41; S.E. Denmark, R.A. Stavenger, J.Am.Chem.Soc.2000, 122, 8837-8847; S.E.Denmark, Y.-P.Su, Y.Nishigaichi, D.M.Coe, K.T.Wong, S.B.D.Winter, J.Y.Choi, J.Org . Chem. 1999, 64, 1958-1967).

[0055] A.N, the synthesis of N'-diprimary alkyl-1,2-cyclohexanediamine (formula (V))

[0056] 1) Synthesis of (1R, 2R)-N, N'dibenzyl-1,2-cyclohexanediamine 2

[0057] In a 250 mL three-neck round bottom flask equipped with a calcium chloride drying tube, add (1R,2R)-(-)-1,2-cyclohexanediamine 1 (2.283 g, 20.0 mmol) and...

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Abstract

The invention relates free NH2-group-attached chiral phosphoramides, a chiral N-phosphonimines and the methods for forming the same. The free NH2-group-attached chiral phosphoramides, having the structure of formula (I) wherein R1 and R2 are independently any organic groups.

Description

technical field [0001] The invention relates to the design and synthesis of a novel chiral imine reagent, which can be used to prepare chiral drugs and their precursors. The present invention includes amino-linked chiral phosphoramides, corresponding chiral N-phosphoramidites and their preparation methods. The chiral N-phosphoramidites are prepared from novel chiral phosphoramides. technical background [0002] In asymmetric synthesis, chiral imine chemistry has been one of the most active topics, because the discovery and development of drugs is very dependent on the functionality of amines. (F.A. Davis, P. Zhou, B.C. Chen, Chem. Soc. Rev. 1998, 27, 13-18). Over the past few decades, this field has been explored by Davis (F.A. Davis, B. Yang, J. Am. Chem. Soc. 2006, 127, 8938-8407; F.A. Davis, R. E. Reddy, J.M. Szewczyk, G.V. Reddy, P. S. Potonovo, H. Zhang, D. T. Reddy, P. Zhou, P. Carroll, J. Org. Chem. 1997, 62, 2555-2563), Ellman (D. A. Cogan, G. C. Liu, K. J. Kim, B....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6584
CPCC07F9/65848
Inventor 孙祥祯李桂根
Owner NOWA PHARMA
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