Selective reduction of a carboxyl group with diborane. Synthesis of specifically carbon-14 labelled D,L-2-Amino-4-(2-aminoethoxy)butanoic acid

1978 ◽  
Vol 56 (22) ◽  
pp. 2853-2855 ◽  
Author(s):  
Yu-Ying Liu ◽  
Edna Thom ◽  
Arnold A. Liebman
Keyword(s):  
Thionyl Chloride ◽  
Title Compound ◽  
Selective Reduction ◽  
Carboxyl Group ◽  
Butanoic Acid ◽  
Carbon 14 ◽  
Sodium Ethyl ◽  
Work Up ◽  
Specific Labelling

Specific labelling of the title compound was achieved through intermediate 3a, methyl 2-(2-phthalimidoethoxy)acetate, derived from methyl bromoacetate-2-14C. Conversion to the corresponding acid (4) was followed with selective diborane reduction which provided 2-(2-phthalimidoethoxy)ethanol-2-14C (5). Treatment with thionyl chloride yielded the chloride 6 which is identical with the intermediate used in the nonlabelled synthesis and reaction with sodium ethyl phthalimidomalonate provided the title compound after hydrolytic work-up.

The inner salt 4-carboxy-2-(pyridinium-4-yl)-1H-imidazole-5-carboxylate monohydrate

2006 ◽  
Vol 62 (7) ◽  
pp. o2751-o2752 ◽  
Author(s):  
Ting Sun ◽  
Jian-Ping Ma ◽  
Ru-Qi Huang ◽  
Yu-Bin Dong
Keyword(s):  
Carboxylic Acid ◽  
Dihedral Angle ◽  
Title Compound ◽  
Acid Group ◽  
Planar Structure ◽  
Carboxyl Group ◽  
Carboxylic Acid Group ◽  
Pyridyl Group ◽  
Compound C

In the title compound, C10H7N3O4·H2O, one carboxyl group is deprotonated and the pyridyl group is protonated. The inner salt molecule has a planar structure, apart from the carboxylic acid group, which is tilted from the imidazole plane by a small dihedral angle of 7.3 (3)°.

scholarly journals (R)-Baclofen [(R)-4-amino-3-(4-chlorophenyl)butanoic acid]

2022 ◽  
Vol 78 (1) ◽  
Author(s):  
Feodor Belov ◽  
Alexander Villinger ◽  
Jan von Langermann
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Title Compound ◽  
Single Crystal Xrd ◽  
Butanoic Acid ◽  
Orthorhombic Crystal ◽  
Orthorhombic Crystal Structure ◽  
Space Group ◽  
Structure Space

This article provides the first single-crystal XRD-based structure of enantiopure (R)-baclofen (form C), C10H12ClNO2, without any co-crystallized substances. In the enantiopure title compound, the molecules arrange themselves in an orthorhombic crystal structure (space group P212121). In the crystal, strong hydrogen bonds and C—H ... Cl bonds interconnect the zwitterionic molecules.

scholarly journals Methyl 1-benzyl-5-methyl-2,4-diphenyl-1H-pyrrole-3-carboxylate

2014 ◽  
Vol 70 (3) ◽  
pp. o338-o339
Author(s):  
Justin M. Lopchuk ◽  
Gordon W. Gribble ◽  
Jerry P. Jasinski
Keyword(s):  
Title Compound ◽  
Pyrrole Ring ◽  
Dihedral Angles ◽  
Carboxyl Group ◽  
Compound C ◽  
Phenyl Rings ◽  
The Mean

In the title compound, C26H23NO2, the dihedral angles between the pyrrole ring and the two phenyl rings are 58.1 (6) and 71.5 (5)°. The mean planes of the 5-methylbenzene ring and the carboxyl group are twisted by 89.5 (3) and 22.1 (9)°, respectively, from the pyrrole ring. In the crystal, weak C—H...O interactions lead to supramolecular layers in theabplane.

scholarly journals (R)-3-(tert-Butoxycarbonyl)-5-methyl-1,2,3-oxathiazolidine 2,2-dioxide

IUCrData ◽  
2017 ◽  
Vol 2 (6) ◽  
Author(s):  
Gerhard Laus ◽  
Klaus Wurst ◽  
Sven Nerdinger ◽  
Frank Richter ◽  
Herwig Schottenberger
Keyword(s):  
Thionyl Chloride ◽  
Title Compound ◽  
Three Dimensional ◽  
Asymmetric Unit ◽  
Sodium Metaperiodate ◽  
Subsequent Oxidation ◽  
Compound C ◽  
Dimensional Network ◽  
Independent Molecules

The chiral title compound, C8H15NO5S, was obtained by cyclization of (R)-1-(tert-butoxycarbonylamino)-2-propanol with thionyl chloride and subsequent oxidation with sodium metaperiodate/ruthenium(IV) oxide. It crystallizes with two independent molecules in the asymmetric unit. In the crystal, C—H...O interactions link the molecules into a three-dimensional network.

scholarly journals Febuxostat ethanol monosolvate

2020 ◽  
Vol 76 (6) ◽  
pp. 816-819
Author(s):  
Thomas Gelbrich ◽  
Volker Kahlenberg ◽  
Verena Adamer ◽  
Sven Nerdinger ◽  
Ulrich J. Griesser
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Title Compound ◽  
Chain Structure ◽  
Hydroxyl Group ◽  
Carboxyl Group ◽  
Hydrogen Bond Donor ◽  
Ethanol Molecule ◽  
Hydrogen Bonded

The title compound, 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic acid ethanol monosolvate, C16H16N2O3S·C2H6O, (I), displays intermolecular O—H...O and O—H...N bonds in which the carboxyl group of the febuxostat molecule and the hydroxyl group of the ethanol molecule serve as hydrogen-bond donor sites. These interactions result in a helical hydrogen-bonded chain structure. The title structure is isostructural with a previously reported methanol analogue.

scholarly journals 4-[(2-Carboxyethyl)amino]benzoic acid monohydrate

2012 ◽  
Vol 68 (4) ◽  
pp. o1098-o1098 ◽  
Author(s):  
Chunman Jia ◽  
Shangwen Chen ◽  
Wenbing Yuan
Keyword(s):  
Hydrogen Bonds ◽  
Benzoic Acid ◽  
Title Compound ◽  
Organic Molecule ◽  
Organic Molecules ◽  
Carboxyl Groups ◽  
Water Molecules ◽  
Carboxyl Group ◽  
Compound C ◽  
Amino Benzoic Acid

In the title compound, C10H11NO4·H2O, the carboxyl group is twisted at a dihedral angle of 6.1 (3)° with respect to the benzene ring. In the crystal, the organic molecules are linked by pairs of O—H...O hydrogen bonds involving both carboxyl groups, forming zigzag chains propagating along theb-axis direction. The water molecules form [100] chains linked by O—H...O hydrogen bonds. The organic molecule and water chains are cross-linked by N—H...Owaterand Owater—H...O hydrogen bonds, generating (001) sheets.

scholarly journals Propyl Gallate

Molbank ◽  
10.3390/m1201 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1201
Author(s):  
Van Hai Nguyen ◽  
Minh Ngoc Le ◽  
Hoa Binh Nguyen ◽  
Kieu Oanh Ha ◽  
Thai Ha Van Pham ◽  
...  
Keyword(s):  
Propyl Gallate ◽  
Thionyl Chloride ◽  
Title Compound ◽  
2D Nmr ◽  
Hydrogen Sulfate ◽  
Economical Method ◽  
Potassium Hydrogen ◽  
Pharmaceutical Industries ◽  
Fischer Esterification ◽  
First Time

The title compound, propyl gallate (III), is an important substance popularly used in the food, cosmetic and pharmaceutical industries. Current chemical syntheses of this compound are based on the acylation supported by thionyl chloride, DIC/DMAP or Fischer esterification using a range of homogenous and heterogenous catalysts. In this paper, an efficient, green, straightforward, and economical method for synthesizing propyl gallate using potassium hydrogen sulfate, KHSO4, as the heterogenous acidic catalyst has been developed for the first time. In addition, this paper provides a comprehensive spectral dataset for the title compound, especially the new data on DEPT and 2D NMR (HSQC and HMBC) spectra which are not currently available in the literature.

scholarly journals Di-μ-nitrato-bis(μ-octaethyl pyrophosphoramide)bis[aquadinitratocalcium(II)]

2021 ◽  
Vol 77 (8) ◽  
pp. 795-798
Author(s):  
Duncan Micallef ◽  
Ulrich Baisch
Keyword(s):  
Hydrogen Bonds ◽  
Water Molecule ◽  
Title Compound ◽  
Bidentate Ligand ◽  
Side Product ◽  
Monoclinic Space Group ◽  
Nitrate Anion ◽  
Asymmetric Unit ◽  
Nitrate Ions ◽  
Work Up

The title compound, di-μ-nitrato-κ3 O,O′:O;O:O,O′-bis(μ-octaethyl pyrophosphoramide-κ2 O:O′)bis[aquabis(nitrato-κ2 O,O′)calcium(II)], [Ca2(NO3)4(C16H40N4O3P2)2(H2O)2] was obtained as a side product during the work up of the synthesis of octaethyl pyrophosphoramide and represents the first structurally characterized complex of this ligand. The compound crystallizes in the monoclinic space group P21/n and the asymmetric unit contains one pyrophosphoramide molecule and one Ca2+ ion coordinated to two nitrate ions and one water molecule. The complex exists as a dimer with a centre of inversion located between two eight-coordinate calcium(II) centres, which are bridged by two nitrate ions and two octaethyl pyrophosphoramide ligands. Each Ca2+ cation is also coordinated to a further nitrate anion, acting as a bidentate ligand, and a water molecule. The complexes stack parallel to the a axis and are held in place by a network of intermolecular O—H...O hydrogen bonds also running parallel to a.

scholarly journals Synthesis and crystal structure of allyl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate

2021 ◽  
Vol 77 (4) ◽  
pp. 331-334
Author(s):  
Vanessa Nowatschin ◽  
Christian Näther ◽  
Ulrich Lüning
Keyword(s):  
Title Compound ◽  
Allyl Bromide ◽  
Carboxyl Group ◽  
X Ray Diffraction ◽  
Synthesis And Crystal Structure ◽  
X Ray ◽  
Compound C ◽  
Pure Phase ◽  
Flash Column Chromatography ◽  
Diethylamino Group

The title compound, C17H19NO4, was synthesized by the reaction of 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylic acid with allyl bromide and purified by flash column chromatography on silica gel. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from acetone. The aromatic core of the molecule is not planar with the diethylamino group and with the carboxyl group that are rotated out of the 2-oxo-2H-chromene plane by 6.7 (2)° and 11.4 (2)°. The NC2 unit of the diethylamino group is planar with an angle sum close to 360°. Intermolecular Car—H...Ocarbonyl interactions lead to the formation of chains parallel to the b axis. X-ray powder diffraction analysis proves that the title compound was obtained as a pure phase.

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