Dicyclohexyl carbodiimide DCC

A recent report describes the conversion of A-formyl- and N-acetyl-L-leucine into optically active azlactones with dicyclohexyl-carbodiimide (DCC) [Eq. (29)]. Other cyclization reagents, e.g. acetic anhydride, POCI3, SOCI2, and polyphosphoric acid, cause racemiza-tion. These azlactones react with optically active amino acid esters to give esters of dipeptides with retention of activity. 

Mechanism of amide formation by reaction of a carboxylic acid and an amine with dicyclohexyl-carbodiimide (DCC). 

Capaccio et al. (2005) used the N-H fulleropyrrolidine derivative to couple long-chain biotin to the Cgo using the carbodiimide dicyclohexyl carbodiimide (DCC) in a pyridine/DMF/C C solvent mixture and reacting overnight at room temperature. This derivative was prepared using a hydrophobic, aliphatic long-chain biotin, but similar derivatives could be prepared... 

Dissolve 6.18g of dicyclohexyl carbodiimide (DCC Chapter 3, Section 1.4) in 10ml of ethyl acetate and add it to the NHS/palmitic acid solution. 

In 1974 the first example of asymmetric induction in an intramolecular Pummerer reaction was observed and reported. Stridsberg and AUenmark (300) treated optically pure o-benzylsulfinylbenzoic acid 271 with acetic anhydride in the presence of dicyclohexyl-carbodiimide (DCC) and found that the Pummerer reaction product, 3,l-benzoxathian-4-one 272, was optically active. The sign and optical rotation values ([alp varied from +42° to -11°) of 272... 

Reducing sugars on treatment with dicyclohexyl carbodiimide (DCC) undergo rearrangement to form a mixture... 

N-Methoxycarbonyl-isothioCyanat (aus Kaliumisothiocyanat und Kohlensaure-chlorid-me-thylester) liefert mit o-Diamino-arenetl in Gegenwart von Dicyclohexyl-carbodiimid (DCC) 2-Methoxycarbonylamino-benzimidazole z. B. 5-(4-Fluor-benzoyl)-2-methoxycarbonylamino-benzimidazol (55% Schmp. > 300°)3OS a 2S8 ... 

The dimethyl sulfoxide (Me2SO)-dicyclohexyl carbodiimide (DCC) method described by Pfitzner and Moffatt24 opened a route to keto derivatives of aldopentosylpyrimidines,2,25 as well as to many keto derivatives of hexosyl-purines3,7,26-31 and -pyrimidines.30,32,33 An alternative proposed by Swern and coworkers,34 requiring the presence of oxalyl chloride as an activating agent, has been used to prepare 4-keto-lyxo-hexose C-nucleosides.13... 

Dicyclohexyl carbodiimide (DCC) is one of the most frequently used coupling agents, especially in organic synthesis applications. It has been used for peptide synthesis since... 

The above obtained [(4S)-4-Methyl-5-oxo-2-(tribromomethyl)-l,3-dioxolan-4-yl]acetic acid (102.5 mg 0.250 mmol) and 2-mercaptopyridine- N-oxide (34.4 mg 0.280 mmol) were suspended in CBrCI3 (1.5ml). The reaction mixture was heated to reflux and a solution of dicyclohexyl carbodiimide (DCC) (103 mg 0.500 mmol) in CBrCI3 (1.0 ml) was added slowly over the course of 30 min. The reaction mixture was stirred for an additional hour. The product was purified by silica gel chromatography (CH2CI2/hexanes (1 2)) and was obtained as white needles from the same solvents. Yield 72 mg (65%) mp 110-113°C. 

As the last example of an SN reaction at the carboxyl carbon of a carbonic acid derivative, consider the synthesis of dicyclohexylurea in Figure 6.30. In this synthesis two equivalents of cyclohexylamine replace the two methoxy groups of dimethyl carbonate. Dicyclohexylurea can be converted into the carbodhmide dicyclohexyl-carbodiimide (DCC) by treatment with tosyl chloride and triethylamine. Thereby, the urea is effectively dehydrated. The mechanism of this reaction is identical to the mechanism that is presented in Figure 7.5 for the similar preparation of a different carbodiimide. 

Although there are many methods available, there are two main routes for the synthesis of nucleoside monophosphates. These involve either the reaction of the nucleoside with 2-cyanoethylphosphate in the presence of a condensing agent such as dicyclohexyl carbodiimide (DCC)2,3 or phosphorylation of the nucleoside... 

Add a small, dry magnetic stirrer bar, followed by N, N -dicyclohexyl carbodiimide (DCC, 1.55 g, 7.5 mmol) and the 5 -0 and N-protected nucleoside (0.5 mmol). Reseal the flask (Caution DCC is an extreme irritant—weigh in fume cupboard, wear gloves). 

Shake base-washed MBHA-resin for 30 min with 2 eq of t-Boc-amino acid and 2 eq of dicyclohexyl carbodiimide (DCC). 

Topliss reductively cyclized JV-(2-nitro-4-chlorophenyl)-JV-inethyl-2-benzo-ylbenzamide to dibenzo[b,/]-l,4-diazocine 10(67JMC642 68USP3409608). Cyclodehydration of N-(2-aminoethyl)-lV-2-(4-chlorobenzoyl)benzylben-zenesulfonamide afforded tetrahydro-2,5-benzodiazocine II (67JOC3270 70USP3496164). Cyclization of the diamino acids 12 using dicyclohexyl-carbodiimide (DCC) resulted in formation of benzodiazocines 13. Com-... 

This complex (1) is obtained as red diamagnetic crystals by refluxing dicyclohexyl-carbodiimide (DCC) with Fe2(CO)6 in heptane for three days. 

The 5-nitro substituted dipeptide analogue was formed by selective reduction (BH,) of methyl 3-amidocarbonyll-5-nitrobenzoate, followed by deesterification (LiOH in THF) and reaction sequentially with Fmoc-Asp-(tBu)-OH and H-Gly-Asp(tBu -Gly-OH (dicyclohexyl carbodiimide (DCC), N-hydroxysuccinimide) to yield Fmoc-Asp(tBu)-5N023 amb-Gly-Asp (tBu)-GlyOH. CycUzation with 4-dimethylaminopyridine (DMAP) and 2-lH-benzotriazole-1-yl-l, 1,3,3,-tetramethyluronium tetrafluoroborate (TBTU) was achieved in 70% yield, followed by reduction (Hj, Pd/C) to give the amino-substituted peptide loop 2. (p. 2681)... 

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