1148-11-4Relevant articles and documents
The formation of a novel Pd/C-ethylenediamine complex catalyst: Chemoselective hydrogénation without deprotection of the o-benzyl and ZV-Cbz groups
Sajiki, Hironao,Hattori, Kazuyuki,Hirota, Kosaku
, p. 7990 - 7992 (1998)
A Pd/C catalyst formed an isolable complex with ethylenediamine employed as the catalytic poison via one-to-one interaction between Pd metal and ethylenediamine, and this complex catalyst [Pd/ C(en)] chemoselectively hydrogenated a variety of reducible functionalities such as olefin, acetylene, nitro, benzyl ester, and azido in the presence of an O-benzyl or N-Cbz protective group. These findings reinforce the versatility potential of O-benzyl and N-Cbz as protective groups in organic synthesis, and the Pd/C(en) catalyst has been identified as a novel and chemoselective catalyst for the hydrogénation.
Synthesis, antitumor activity, and nephrotoxicity of the optical isomers of 2-aminomethylpyrrolidine(1,1-cyclobutane-dicarboxylato) platinum(II)
Morikawa,Honda,Endoh -i.,Matsumoto,Akamatsu -i.,Mitsui,Koizumi
, p. 837 - 842 (1991)
The optical isomers of 2-aminomethylpyrrolidine(1,1-cyclobutane-dicarboxylato)platinum(II) (DWA2114, 1), which has potent antitumor activity against various tumors, were synthesized. They were examined for antitumor activity against Colon 26 carcinoma in a sc-iv system, and changes in urinary protein and sugar levels in drug-treated mice were used as an index of nephrotoxicity. In their effect on tumors, (+)-(S)-2-aminomethylpyrrolidine(1,1-cyclobutanedicarboxylato) platinum(II) (6b) was more potent than the enantiomer 6a in that the effective dose of 6b was smaller than that of 6a; but, both drugs exhibited potent antitumor activity. On the other hand, a distinct difference between 6a and 6b was shown in their nephrotoxicity. Isomer 6b induced a great increase in urinary protein and sugar levels in mice, whereas 6a caused no increase in these levels.
Microwave spectroscopy of the twist C(β)-exo/C(γ)-endo conformation of prolinamide
Kuhls, Kimberly A.,Centrone, Charla A.,Tubergen, Michael J.
, p. 10194 - 10198 (1998)
The rotational transitions of three isotopomers of prolinamide were measured with a Fourier-transform microwave spectrometer. A twist pyrrolidine ring conformation with C(β)-exo and C(γ)-endo reproduces the experimental moments of inertia. Stark-effect measurements of five [M] components were used to determine that the dipole moment of this conformation of prolinamide is 3.83(4) D. Kraitchman's method of isotopic substitution was used to determine an N-N distance of 2.684(2) A?.
Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations
Takeuchi,Yamada,Suzuki,Koizumi
, p. 225 - 232 (1996)
2-Ethenylpyrrolidine derivative 8b was prepared from N-protected proline ethyl ester 6b. Bromofluorination of 8b wth NBS-Bu4NF/2HF gave a 1:1 regioisomeric mixture, 9b and 10b (X = Br). Dehydrobromination of 9b and 10b with t-BuOK produced a fluoroolefin 11 and a proline amide isostere model 12, respectively. Deprotection of the Z group in 12 was attempted by treatment with CF3COOH. Although formation of the useful molecule is pseudopeptide synthesis, 13, was observed as checked by NMR spectra, it seemed to decompose slowly during purification procedure to give a mixture of fluorine-free compounds.
Rational design of asymmetric organocatalysts - Increased reactivity and solvent scope with a tetrazolic acid
Hartikka, Antti,Arvidsson, Per I.
, p. 1831 - 1834 (2004)
Replacement of the carboxylic acid functionality in the widely used organocatalyst proline with a tetrazolic acid leads to a catalyst with increased reactivity and solvent scope, as demonstrated in the direct catalytic asymmetric aldol reaction.
Radical cyclization of β-aminoacrylates: Stereoselective synthesis of indolizidines 167B and 209D
Lee, Eun,Li, Kap Sok,Lim, Jaehong
, p. 1445 - 1446 (1996)
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Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form
Katakam, Nanda Kumar,Seifert, Cole W.,D'Auria, John,Li, Guigen
, p. 604 - 613 (2019/08/01)
Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.
PROCESS AND INTERMEDIATES FOR SYNTHESIS OF PEPTIDE COMPOUNDS
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Paragraph 0163; 0164, (2019/02/13)
Disclosed is a new process and intermediates for preparing dipyrrolidine peptide compounds such as, for example, rapastinel. Advantageously, the process may be industrially scalable and cost-effective and use less toxic reagents and/or solvents. Further, the process may be used to prepare peptide compounds having improved purity.