70183-69-6Relevant academic research and scientific papers
Mild one-pot conversion of carboxylic acids to amides or esters with Ph3P/trichloroisocyanuric acid
Rodrigues, Rogério Da C.,Barros, Igor M. A.,Lima, Edson L. S.
, p. 5945 - 5947 (2005)
The reaction of trichloroisocyanuric acid (TCICA) and triphenylphosphine in the presence of a carboxylic acid results in the in situ formation of the corresponding acid chloride under mild conditions. Subsequent addition of amines or alcohols, in the presence of a tertiary amine affords the corresponding amides, or esters, in good to excellent yields. The methodology was applied to the synthesis of a dipeptide.
Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D
Snider, Barry B.,Song, Fengbin,Foxman, Bruce M.
, p. 793 - 800 (2007/10/03)
The first synthesis of (±)-anchinopeptolide D (4) has been accomplished in seven steps in 10% overall yield from octopamine hydrochloride (17), N-(Boc)glycine (16), and 5-amino-2-hydroxypentanoic acid (22). The key step is the aldol dimerization and hemiaminal formation of α-keto amide 26, which gives primarily protected anchinopeptolide D 27 under kinetically controlled conditions. Cycloanchinopeptolide D (31) has been prepared by the unprecedented head-to-head photodimerization of the two hydroxystyrylamides of 4 using the hydrophobic effect in water to force the two side chains into close proximity so that [2 + 2] cycloaddition is faster than trans to cis double bond isomerization. Coupling of amine 21 with pyroglutamic acid affords the naturally occurring tripeptide 35, which had been assigned glutamic acid structure 34.
THE SYNTHESES OF N-FREE α-DEHYDROAMINO ACID ESTERS AND N-ACETYL DEHYDRODIPEPTIDE ESTER FROM N-CARBOXY α-DEHYDROAMINO ACID ANHYDRIDE
Shin, Chung-gi,Yonezawa, Yasuchika,Yoshimura, Juji
, p. 1635 - 1638 (2007/10/02)
N-Carboxy α-dehydroamino acid anhydride, derived from N-benzyloxycarbonyl α-dehydroamino acid (DHA) and thionyl chloride, was found to be very useful for the synthesis of N-free DHA ester by alcoholysis and N-acetyl dehydrodipeptide ester by coupling was
