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Record W4396599404 · doi:10.1002/chir.23672

New methods for resolution of hydroxychloroquine by forming diastereomeric salt and adding chiral mobile phase agent on RP‐HPLC

2024· article· en· W4396599404 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueChirality · 2024
Typearticle
Languageen
FieldChemistry
TopicAnalytical Chemistry and Chromatography
Canadian institutionsDalhousie University
FundersNational Natural Science Foundation of China
KeywordsChemistryDiastereomerEnantiomerHigh-performance liquid chromatographyResolution (logic)ChromatographyYield (engineering)Enantiomeric excessTartaric acidStereochemistryOrganic chemistryCitric acidEnantioselective synthesis

Abstract

fetched live from OpenAlex

Abstract Hydroxychloroquine (HCQ), 2‐([4‐([7‐Chloro‐4‐quinolyl]amino)pentyl]ethylamino)ethanol, exhibited significant biological activity, while its side effects cannot be overlooked. The RP‐HPLC enantio‐separation was investigated for cost‐effective and convenient optical purity analysis of HCQ. The thermodynamic resolution of Rac‐HCQ, driven by enthalpy and entropy, was achieved on the C18 column using Carboxymethyl‐β‐cyclodextrin (CM‐β‐CD) as the chiral mobile phase agent (CMPA). The effects of C CM‐β‐CD , pH, and triethylamine (TEA) V% on the enantio‐separation process were explored. Under the optimum conditions at 24°C, the retention times for the two enantiomers were and , resulting in . The resolution via diastereomeric salt formation of Rac‐HCQ was developed to obtain the active pharmaceutical ingredient of single enantiomer S‐HCQ. Di‐p‐Anisoyl‐L‐Tartaric Acid (L‐DATA) was proved effective as the resolution agent for Rac‐HCQ. Surprisingly, it was found that refluxing time was a key fact affecting the resolution efficiency, which meant the kinetic dominate during the process of the resolution. Four factors—solvent volume, refluxing time, filtration temperature, and molar ratio—were optimized using the single‐factor method and the response surface method. Two cubic models were established, and the reliability was subsequently verified. Under the optimal conditions, the less soluble salt of 2L‐DATA:S‐HCQ was obtained with a yield of 96.9% and optical purity of 63.0%. The optical purity of this less soluble salt increases to 99.0% with a yield of 74.2% after three rounds recrystallization.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.228
Threshold uncertainty score0.757

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.024
GPT teacher head0.368
Teacher spread0.344 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it