Ethyl N-(diphenylmethylene)glycinate

Chemical Properties

white to light yellow crystalline powder or

Uses

N-(Diphenylmethylene)glycine Ethyl Ester is used as a reagent in the synthesis of pyrazolopyrrolyl tetrahydropyran DPP-4 inhibitors.

Application

Ethyl N-(diphenylmethylene)glycinate features a diphenylmethylene group that enhances its reactivity and stability, making it particularly useful in organic synthesis and pharmaceutical development.

Reactions

Ethyl N-(diphenylmethylene)glycinate undergoes monoalkylations, dialkylations and Michael additions to ethylenic and acetylenic acceptors under appropriate solid-liquid phase transfer catalysis conditions. Further transformations of the α-disubstituted ketimines lead to α-alkylated aspartic and glutamic acid derivatives.

Synthesis

Ethyl N-(diphenylmethylene)glycinate is prepared by transimination of Benzophenone Imine with alkyl glycinate hydrochloride (room temperature/CH2Cl2).

References

[1] Patent: EP1422220, 2004, A1. Location in patent: Page 5
[2] Patent: CN104557684, 2017, B. Location in patent: Paragraph 0021-0026; 0027; 0028; 0029; 0030-0033
[3] Tetrahedron Letters, 2005, vol. 46, # 16, p. 2795 - 2797
[4] Patent: US2010/173777, 2010, A1. Location in patent: Page/Page column 23
[5] Patent: WO2016/27285, 2016, A2. Location in patent: Page/Page column 50; 51