LXVII.—The isomeric tropic acids

McKenzie, Alex.; Wood, John Kerfoot

doi:10.1039/ct9191500828

Cited by 17 publications

(8 citation statements)

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“…With carbon‐14–labeled racemic tropic acid in hand, a crystallization process was developed to separate the ( S )‐enantiomer or l ‐tropic acid along with a chiral high‐performance liquid chromatography (HPLC) method. It is worth mentioning that enzymatic chiral resolution of tropic acid has been reported . Different solvent systems were used to evaluate the chiral separation of racemic tropic acid using d ‐(−)‐ threo ‐2‐amino‐1‐(4‐nitrophenyl)‐1,3‐propanediol ( 8 ) as a resolving reagent .…”

Section: Resultsmentioning

confidence: 99%

“…It is worth mentioning that enzymatic chiral resolution of tropic acid has been reported. [25][26][27] Different solvent systems SCHEME 3 Separation of (S)-tropic acid-carboxyl-14 C FIGURE 2 (Top) Chiral high-performance liquid chromatography of l-tropic acid and (bottom) d-tropic acid isolated from the mother liquor were used to evaluate the chiral separation of racemic tropic acid using D-(−)-threo-2-amino-1-(4-nitrophenyl)-1,3propanediol (8) as a resolving reagent. 28 In our hands, the best separation of the (S)-isomer from the mixture was achieved in either water or isopropanol solvent systems.…”

Section: Resultsmentioning

confidence: 99%

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Buscopan labeled with carbon‐14 and deuterium

Latli

Stiasni

Hrapchak

et al. 2016

Labelled Comp Radiopharmac

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Hyosine butyl bromide, the active ingredient in Buscopan, is an anticholinergic and antimuscarinic drug used to treat pain and discomfort caused by abdominal cramps. A straightforward synthesis of carbon-14- and deuterium-labeled Buscopan was developed using scopolamine, n-butyl-1- C bromide, and n-butyl- H bromide, respectively. In a second carbon-14 synthesis, the radioactive carbon was incorporated in the tropic acid moiety to follow its metabolism. Herein, we describe the detailed preparations of carbon-14- and deuterium-labeled Buscopan.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Buscopan labeled with carbon‐14 and deuterium

Latli

Stiasni

Hrapchak

et al. 2016

Labelled Comp Radiopharmac

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“…Atropic acid was prepared by vacuum distillation of atrolactinic acid (the method of McKenzie and Wood). 14 3.00 grams of atrolactinic acid were placed in a 100 ml round bottom flask attached via a short length of glass pipe to a 50 ml round bottom collection flask which was connected to a gas-vacuum manifold. While under strong vacuum the flask containing the atrolactinic acid was heated by flame; after 5 min a powdery white residue began to collect on the sides of the collection flask.…”

Section: Methods For Synthesis Of Atropic Acidmentioning

confidence: 99%

Neoteric solvents for asymmetric hydrogenation: supercritical fluids, ionic liquids, and expanded ionic liquidsThis work was presented at the Green Solvents for Catalysis Meeting held in Bruchsal, Germany, 13–16th October 2002.

et al. 2003

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“…The synthesis of tropic acid from acetophenone was reported by McKenzie and Wood in 1920. In a key step of the synthesis, atropic acid (2-phenylpropenoic acid) is reacted with hydrochloric acid in diethyl ether with heating for 24 h to produce β-chlorohydratropic acid (3-chloro-2-phenylpropanoic acid), as shown in Scheme .…”

Section: Introductionmentioning

confidence: 99%

Molecular Modeling of an Electrophilic Addition Reaction with “Unexpected” Regiochemistry

Best

Helms

2017

J. Chem. Educ.

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The electrophilic addition of a hydrohalic acid (HX) to an alkene is often one of the first reactions learned in second-year undergraduate organic chemistry classes. During the ensuing discussion of the mechanism, it is shown that this reaction follows Markovnikov’s rule, which states that the hydrogen atom will attach to the carbon with fewer substituents while the halogen atom will attach to the carbon with more substituents. However, in the preparation of tropic acid, the reaction of HCl with atropic acid (2-phenylpropenoic acid) does not follow this rule because it is a conjugated system. Molecular modeling of the possible carbocation intermediates suggests that the reaction follows a conjugate addition mechanism involving a 1,4-addition of HCl across the conjugated alkene and carboxyl group rather than addition across the alkene as students often first propose. PM3 semiempirical calculations are used to determine the energies of three possible carbocation intermediates. The energies obtained from the modeling suggest that the carbocation intermediate produced by the 1,4-addition is the most stable.

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LXVII.—The isomeric tropic acids

Cited by 17 publications

References 0 publications

Buscopan labeled with carbon‐14 and deuterium

Buscopan labeled with carbon‐14 and deuterium

Neoteric solvents for asymmetric hydrogenation: supercritical fluids, ionic liquids, and expanded ionic liquidsThis work was presented at the Green Solvents for Catalysis Meeting held in Bruchsal, Germany, 13–16th October 2002.

Molecular Modeling of an Electrophilic Addition Reaction with “Unexpected” Regiochemistry

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