HMDS-promoted in situ amidation reactions of carboxylic acids and amines

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3419-3422

  Chou, Wen Chih ^a   Chou, Ming Chen ^a   Lu, Yann Yu ^a   Chen, Shyh Fong ^a  

^a Developmental Center for Biotechnology   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,1,3,3,3 HEXAMETHYLDISILAZANE; AMINE; CARBOXYLIC ACID DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0033597262     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00505-5     Document Type: Article

References (27)

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25. 10. The silyl ester of 1b was prepared by treating 1b with HMDS at 110 °C for 2 h, and its subsequent reaction with piperazine at 110 °C for 5 h yielded the desired amide 4.
26. 11. TMSCl has been used to catalyze the estification of carboxylic acids. Nakao, R.; Oka, K.; Fukumoto, T. Bull. Chem. Soc. Jpn. 1981, 54, 1267.
27. 23 -18.5° (c 0.2, MeOH)) was determined to be 91% by HPLC analysis with chiral stationary phase (Chiralcel OJ column (Daicel) using 2-propanol:n-hexane, 1:10 as the eluent) and also compared with the sample (prepared at 0 °C by using BOP-Cl as the coupling reagent).