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can be used. Because the reaction is mild, esters can be obtained that are inaccessible through other methods for instance esters of the sensitive 2,4-dihydroxybenzoic acid. A characteristic is the formal uptake of water generated in the reaction by DCC, forming the
167:. If the esterification is slow, a side-reaction occurs, diminishing the final yield or complicating purification of the product. This side-reaction is a 1,3-rearrangement of the
257:
W. König, R. Geiger (1970). "Eine neue
Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1-Hydroxy-benzotriazolen".
178:
which is unable to further react with the alcohol. DMAP suppresses this side reaction, acting as an acyl transfer-reagent in the following manner:
182:
396:
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331:"Esterification of Carboxylic Acids with Dicyclohexylcarbodiimide/4-Dimethylaminopyridine: tert-Butyl ethyl fumarate"
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82:
98:
203:
121:
201:
B. Neises, W. Steglich (1978). "Simple Method for the
Esterification of Carboxylic Acids".
8:
295:"A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids"
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Jordan, Andrew; Whymark, Kyran D.; Sydenham, Jack; Sneddon, Helen F. (2021).
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J. C. Sheehan, G. P. Hess (1955). "A New Method of
Forming Peptide Bonds".
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in 1978. It is an adaptation of an older method for the formation of
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97:by means of DCC (dicyclohexylcarbodiimide) and
372:Mechanism for the Steglich esterification
354:. 1. Auflage, Wiley-VCH, Weinheim, 2003,
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116:This reaction generally takes place at
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89:. The reaction was first described by
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329:B. Neises and W. Steglich.
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81:as a coupling reagent and
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171:-acyl intermediate to an
145:is described as follows:
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52:Organic Chemistry Portal
46:
21:
397:Esterification reactions
272:10.1002/cber.19701030319
163:because amines are more
79:dicyclohexylcarbodiimide
22:Steglich esterification
83:4-dimethylaminopyridine
71:Steglich esterification
57:steglich-esterification
216:10.1002/anie.197805221
122:polar aprotic solvents
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99:1-hydroxybenzotriazole
204:Angew. Chem. Int. Ed.
109:
73:is a variation of an
244:10.1021/ja01609a099
387:Coupling reactions
312:10.1039/D1GC02251B
143:reaction mechanism
137:Reaction mechanism
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343:Collected Volumes
336:Organic Syntheses
232:J. Am. Chem. Soc.
110:Steglich overview
91:Wolfgang Steglich
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41:Coupling reaction
31:Wolfgang Steglich
16:Chemical reaction
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238:(4): 1067–1068.
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131:dicyclohexylurea
118:room temperature
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75:esterification
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47:Identifiers
27:Named after
381:Categories
350:J. Otera:
299:Green Chem
260:Chem. Ber.
189:References
176:-acylurea
129:compound
101:(HOBT).
87:catalyst
280:5436656
133:(DCU).
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161:amides
157:amines
95:amides
155:With
85:as a
77:with
356:ISBN
276:PMID
141:The
127:urea
69:The
307:doi
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174:N
169:O
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