Amidation of Esters with Amides in the Presence of Methoxide Ion

Allred, Evan L.; Hurwitz, Melvin D.

doi:10.1021/jo01018a063

Cited by 21 publications

(8 citation statements)

References 3 publications

(3 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Attack on the formyl group by the alkoxide ion would then yield the products. 243 This proposal is supported by the isolation of product 127 from the reaction of substituted amino ester 126 and formamide.244 This reaction evidently occurs by way of an N- Mechanistically, this reaction is believed to proceed by way of aldimine 128 (Ri = H) by an amine-amide exchange. The aldimine is then reduced to primary amine 48 (R3 = ; R< = Ar).…”

Section: Addition To Olefinsmentioning

confidence: 99%

Chemistry of formic acid and its simple derivatives

Gibson¹

1969

Chem. Rev.

131

View full text Add to dashboard Cite

Section: Addition To Olefinsmentioning

confidence: 99%

Chemistry of formic acid and its simple derivatives

Gibson¹

1969

Chem. Rev.

131

View full text Add to dashboard Cite

“…The right-hand side of the cystothiazole containing the [2,4‘]-bis(thiazole) moiety was prepared using methodology that we developed for the preparation of thiazoline via an electrophilic activation of amide using triflic anhydride (Tf 2 O) . The isopropylamide 16 was activated with Tf 2 O in the presence of pyridine to afford a pyridinium salt intermediate . Addition of l -cysteine·HCl afforded the thiazoline (+)- 17 in 90% yield.…”

mentioning

confidence: 99%

Total Synthesis of (+)-Cystothiazole A

DeRoy

Charette

2003

Org. Lett.

View full text Add to dashboard Cite

[structure: see text]. The total synthesis of cystothiazole A is described. Key steps of the synthesis include an Evans asymmetric catalytic aldol reaction, which established the required C4-C5 stereochemistry. The [2,4']-bis(thiazole) was obtained applying our methodology of electrophilic activation of amide. Semistabilized Wittig reaction between the phosphonium salt 3 and the aldehyde 2 afforded 1 in nine linear steps and 38% overall yield.

show abstract

“…The requisite amide 28 was found to be easily accessible from ester 25 by a mild amidation reaction with formamide (10 equiv) and sodium methoxide (3 equiv) in THF . This reaction presumably proceeds by nucleophilic attack of the formamide anion to the ester to give a mixed imide, which is cleaved by sodium methoxide to generate the desired amide 28 .…”

Section: Resultsmentioning

confidence: 99%

An Efficient Process for the Manufacture of Carmegliptin

Abrecht

Adam

Bromberger

et al. 2011

Org. Process Res. Dev.

View full text Add to dashboard Cite

A short and high-yielding synthesis of carmegliptin (1) suitable for large-scale production is reported. The tricyclic core was assembled efficiently by a decarboxylative Mannich addition−Mannich cyclization sequence. Subsequent crystallization-induced dynamic resolution of enamine 7 using (S,S)-dibenzoyltartaric acid was followed by diastereoselective enamine reduction to give the fully functionalized tricyclic core with its three stereogenic centers. The C-3 nitrogen was introduced by Hofmann rearrangement of amide 28, and the resulting amine 10 was coupled with (S)-fluoromethyl lactone 31. Following cyclization to lactam 13 and amine deprotection, 1 was obtained in 27−31% overall yield with six isolated intermediates.

show abstract

Amidation of Esters with Amides in the Presence of Methoxide Ion

Cited by 21 publications

References 3 publications

Chemistry of formic acid and its simple derivatives

Chemistry of formic acid and its simple derivatives

Total Synthesis of (+)-Cystothiazole A

An Efficient Process for the Manufacture of Carmegliptin

Contact Info

Product

Resources

About