86194-94-7Relevant academic research and scientific papers
N-carbamate protected amino acid derived guanidine organocatalysts
Al-Taie, Zahraa S.,Anderson, Joseph M.,Bischoff, Laura,Christensen, Jeppe,Coles, Simon J.,Froom, Richard,Gibbard, Mari E.,Jones, Leigh F.,de Kleijne, Frank F.J.,Murphy, Patrick J.,Thompson, Emma C.
, (2021/05/05)
We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poo
COMPOSITIONS CONTAINING, METHODS AND USES OF ANTIBODY-TLR AGONIST CONJUGATES
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Paragraph 00513; 00623; 00628, (2020/08/28)
Disclosed herein are Trastuzumab-linked TLR-agonist derivative analogs that include at least one non-natural amino acid, and methods for making such non-natural amino acids and polypeptides. The Trastuzumab-linked TLR-agonist derivative analogs can includ
A convenient synthesis of 2-acyl benzothiazoles/thiazoles from benzothiazole/thiazole and N,N'-carbonyldiimidazole activated carboxylic acids
Huang, Tonghui,Wu, Xin,Yu, Yongbo,An, Lin,Yin, Xiaoxing
supporting information, p. 1667 - 1670 (2019/06/04)
A convenient and efficient strategy for the synthesis of 2-acyl benzothiazoles/thiazoles has been developed. The treatment of benzothiazole/thiazole with allylic Grignard reagents readily generates the corresponding 2-Grignard reagents, which is followed by a reaction with N,N'-carbonyldiimidazole activated carboxylic acids to afford various 2-acyl benzothiazoles/thiazoles products. The synthetic method is applicable to a wide array of carboxylic acids and allows easy access to 2-acyl benzothiazoles/thiazoles with considerable yields under mild reaction conditions.
Synthesis and preliminary biological evaluations of (+)-isocampholenic acid-derived amides
Gro?elj, Uro?,Golobi?, Amalija,Knez, Damijan,Hrast, Martina,Gobec, Stanislav,Ri?ko, Sebastijan,Svete, Jurij
, p. 667 - 676 (2016/07/12)
The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1S)-(+)-10-camphorsulfonic acid. The novel amines as well as (+)-isocampholenic acid have been used as building blocks in the constru
A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
Ivkovic, Jakov,Lembacher-Fadum, Christian,Breinbauer, Rolf
supporting information, p. 10456 - 10460 (2015/11/10)
N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.
Cu(I)-catalyzed [3+2] cycloadditions of tert-butyl (S)-(3-oxopent-4-yn-2- yl)carbamate to 1-benzylidenepyrazole-3-one-derived azomethine imines
Pusavec, Eva,Mirnik, Jona,Senica, Luka,Groselj, Uros,Stanovnik, Branko,Svete, Jurij
, p. 615 - 626 (2014/06/10)
Parallel screening of suitable reaction conditions for Cu(I)-catalyzed [3+2] cycloadditions of (1Z,4R*,5R*)-4- benzoylamino-1-benzylidene-5-phenyl-3-oxopyrazolidin-1-ium-2-ide (1a) to methyl propiolate (2) has established that this reaction proceeds smoothly at room temperature in acetonitrile in the presence of CuI and Huenig's base. The optimized reaction conditions were then applied in regio- and stereo-selective 1,3-dipolar cycloadditions of racemic azomethine imines 1a-e to tert-butyl (S)-(3-oxopent-4-yn-2-yl)carbamate (6) leading to mixtures of diastereomeric non-racemic chromatographically separable cycloadducts 7a-d, 7′ a-d, 8e, and 8′e. The structures of the products were confirmed by NMR spectroscopy.
Process development and pilot-plant synthesis of (S)-tert-butyl 1-oxo-1-(1-(pyridin-2-yl)cyclopropylamino)propan-2-ylcarbamate: Studies on the scale-up of Kulinkovich-Szymoniak cyclopropanation
Li, Wenjie,Gao, Joe J.,Lorenz, Jon C.,Xu, Jinghua,Johnson, Joe,Ma, Shengli,Lee, Heewon,Grinberg, Nelu,Busacca, Carl A.,Lu, Bruce,Senanayake, Chris H.
experimental part, p. 836 - 839 (2012/08/27)
A practical and scalable synthesis of (S)-tert-butyl 1-oxo-1-(1-(pyridin-2- yl)cyclopropylamino)propan-2-ylcarbamate, an intermediate in the manufacture of a lymphocyte function-associated antigen 1 inhibitor, is described. The titled compound is prepared via an efficient one-pot, two-step telescoped sequence starting from readily available materials. A modified Kulinkovich-Szymoniak cyclopropanation of a nitrile followed by in situ amide formation with an activated carboxylic acid derivative afforded the target product in about 50% overall isolated yield and >97% purity.
Conversion of α-amino acids into bioactive o-aminoalkyl resorcylates and related dihydroxyisoindolinones
Patel, Bhavesh H.,Mason, Andrew M.,Patel, Hetal,Coombes, R. Charles,Ali, Simak,Barrett, Anthony G. M.
experimental part, p. 6209 - 6217 (2011/10/02)
The synthesis of biologically active o-aminoalkyl resorcylates and related dihydroxyisoindolinones from functionalized α-amino acids without the use of phenolic protection is described. The key aminoalkyl-diketo-dioxinone intermediates were prepared utilizing a crossed Claisen condensation reaction in the presence of diethylzinc. The aromatic unit was constructed via late stage cyclization and aromatization, and subsequent modification provided the novel resorcylates which showed activity against a selection of receptors and kinases, including 5-HT and CDK.
Carbonyldiimidazole (CDI) mediated synthesis of Nα- protected amino acid azides: Application to the one-pot preparation of ureidopeptides
Vasantha,Vishwanatha,Sureshbabu, Vommina V.
experimental part, p. 1093 - 1098 (2012/06/01)
Synthesis of Nα-protected amino acyl azides starting from corresponding acids via the carbonyldiimidazole (CDI) activation is described. The protocol is extended for a one-pot preparation of ureido peptides that circumvents the isolation of acy
Synthesis of 3-(pyrimidinyl)pyrrole derivatives
Nestorak, Igor Yu.,Tverdokhlebov, Anton V.,Tolmachev, Andrey A.,Volovenko, Yulian M.
experimental part, p. 611 - 623 (2010/09/07)
Alkylation of 4,6-dimethyl-2-pyrimidineacetonitrile and 2,6-dimethyl-4-pyrimidineacetonitrile with chloroacetic acid anilides was shown to give 5-amino-4-(4,6-dimethyl-2-pyrimidinyl)-2,3-dihydro-1-arylpyrrol-2-ones and 5-amino-4-(2,6-dimethyl-4-pyrimidiny
