Effect of solvent on racemization in carbodiimide mediated solid phase fragment condensations

Alvin C. Haver; D. David Smith

doi:10.1016/S0040-4039(00)77583-6

Effect of solvent on racemization in carbodiimide mediated solid phase fragment condensations

Alvin C. Haver, D. David Smith

Department of Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

The Izumiya tripeptide was used to assess racemization in solid-phase fragment condensations. Boc-Gly-Ala-OH¹ was coupled to Leu-PAM resin DIC in a variety of solvents, both with and without HOBt. After cleavage from the resin, the extent of racemization was determined using C18 RP-HLPC to separate the epimers. Solvents used were DMF, NMP, TFE and each of these as mixtures with DCM. Also tested was a mixture of NMP and DMSO (85:15). Couplings in DMF/DCM (1:1) and NMP/DCM (1:1) in the presence of HOBt were in excess of 98% and racemization was undetectable. (<0.1%).

Original language	English (US)
Pages (from-to)	2239-2242
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(00)77583-6
State	Published - Apr 2 1993

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Effect of solvent on racemization in carbodiimide mediated solid phase fragment condensations",

abstract = "The Izumiya tripeptide was used to assess racemization in solid-phase fragment condensations. Boc-Gly-Ala-OH1 was coupled to Leu-PAM resin DIC in a variety of solvents, both with and without HOBt. After cleavage from the resin, the extent of racemization was determined using C18 RP-HLPC to separate the epimers. Solvents used were DMF, NMP, TFE and each of these as mixtures with DCM. Also tested was a mixture of NMP and DMSO (85:15). Couplings in DMF/DCM (1:1) and NMP/DCM (1:1) in the presence of HOBt were in excess of 98% and racemization was undetectable. (<0.1%).",

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T1 - Effect of solvent on racemization in carbodiimide mediated solid phase fragment condensations

AU - Haver, Alvin C.

AU - David Smith, D.

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N2 - The Izumiya tripeptide was used to assess racemization in solid-phase fragment condensations. Boc-Gly-Ala-OH1 was coupled to Leu-PAM resin DIC in a variety of solvents, both with and without HOBt. After cleavage from the resin, the extent of racemization was determined using C18 RP-HLPC to separate the epimers. Solvents used were DMF, NMP, TFE and each of these as mixtures with DCM. Also tested was a mixture of NMP and DMSO (85:15). Couplings in DMF/DCM (1:1) and NMP/DCM (1:1) in the presence of HOBt were in excess of 98% and racemization was undetectable. (<0.1%).

AB - The Izumiya tripeptide was used to assess racemization in solid-phase fragment condensations. Boc-Gly-Ala-OH1 was coupled to Leu-PAM resin DIC in a variety of solvents, both with and without HOBt. After cleavage from the resin, the extent of racemization was determined using C18 RP-HLPC to separate the epimers. Solvents used were DMF, NMP, TFE and each of these as mixtures with DCM. Also tested was a mixture of NMP and DMSO (85:15). Couplings in DMF/DCM (1:1) and NMP/DCM (1:1) in the presence of HOBt were in excess of 98% and racemization was undetectable. (<0.1%).

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JF - Tetrahedron Letters

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ER -

Effect of solvent on racemization in carbodiimide mediated solid phase fragment condensations

Abstract

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