{"revision":{"id":"prv_xu6zgds6q2","problem_id":"prb_p8918e91ki","revision_number":1,"statement_md":"# Curate this paper into an ORD dataset\n\nBuild an Open Reaction Database (ORD) dataset of the reactions reported in:\n\n- **Paper:** Accelerated Development of a Scalable Ring-Closing Metathesis to Manufacture AMG 176 Using a Combined High-Throughput Experimentation and Computational Modeling Approach\n- **Authors:** Gabrielle St‐Pierre, Alan H. Cherney, Wencan Chen et al.\n- **Published:** OPRD, 2020-11-25\n- **DOI:** [10.1021/acs.oprd.0c00416](https://doi.org/10.1021/acs.oprd.0c00416)\n- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570074)\n\nThe reference input `card` holds these facts, the source-data locations and the notes below in machine-readable form.\n\n## Scope\n\nEvery reaction the paper reports with its data: inputs with amounts and roles, conditions, workups, outcomes and provenance, following the `ord-curation` Skill. Submit one ORD Dataset for the paper; if its data come from several screens or methods, keep them together and say so in the dataset description.\n\n## Source data\n\nThis paper covers HTE plus DFT-guided development of the ring-closing metathesis step (16-membered macrocycle) in the AMG 176 synthesis (OPRD 2020, Amgen/UCLA). The SI on the ACS figshare mirror (labelled CC BY-NC 4.0) contains the HTE RCM procedure and catalyst-screening bar charts with numeric product LCAP labels. Figure SI1 covers about 10 Ru catalysts at 4 mol% with the acetate substrate, and Figure SI2 about 24 catalysts at 1 mol% with the 4-bromobenzoate substrate. The SI also has characterisation of the ester-protected substrates and macrocycles, catalyst structures (Scheme SI1), DFT data and an X-ray structure. The main-text screening and optimisation tables are in the paywalled article. Pitfalls: outcomes are LCAP (HPLC area %), not yields; the substrates are complex stereodefined macrocycle precursors that must be converted to SMILES carefully; the Ru catalysts are identified by trade codes (e.g. M71-SIPr, M73-SIMes, HG2, GreenCat) that must be mapped to structures.\n\nKnown locations:\n\n- [https://acs.figshare.com/articles/journal_contribution/Accelerated_Development_of_a_Scalable_Ring-Closing_Metathesis_to_Manufacture_AMG_176_Using_a_Combined_High-Throughput_Experimentation_and_Computational_Modeling_Approach/13285721](https://acs.figshare.com/articles/journal_contribution/Accelerated_Development_of_a_Scalable_Ring-Closing_Metathesis_to_Manufacture_AMG_176_Using_a_Combined_High-Throughput_Experimentation_and_Computational_Modeling_Approach/13285721): SI PDF op0c00416_si_001.pdf (67 pp): HTE RCM procedure, substrate/macrocycle characterisation, Figure SI1/SI2 catalyst-screen bar charts with numeric LCAP labels, Scheme SI1 catalyst structures, DFT energies and coordinates, NMR spectra (license: CC BY-NC 4.0 as labelled on the ACS figshare mirror)\n- [https://acs.figshare.com/articles/journal_contribution/Accelerated_Development_of_a_Scalable_Ring-Closing_Metathesis_to_Manufacture_AMG_176_Using_a_Combined_High-Throughput_Experimentation_and_Computational_Modeling_Approach/13285724](https://acs.figshare.com/articles/journal_contribution/Accelerated_Development_of_a_Scalable_Ring-Closing_Metathesis_to_Manufacture_AMG_176_Using_a_Combined_High-Throughput_Experimentation_and_Computational_Modeling_Approach/13285724): SI PDF op0c00416_si_002.pdf: X-ray structure report for macrocycle 13 (license: CC BY-NC 4.0 as labelled on the ACS figshare mirror)\n- [https://acs.figshare.com/articles/dataset/Accelerated_Development_of_a_Scalable_Ring-Closing_Metathesis_to_Manufacture_AMG_176_Using_a_Combined_High-Throughput_Experimentation_and_Computational_Modeling_Approach/13285727](https://acs.figshare.com/articles/dataset/Accelerated_Development_of_a_Scalable_Ring-Closing_Metathesis_to_Manufacture_AMG_176_Using_a_Combined_High-Throughput_Experimentation_and_Computational_Modeling_Approach/13285727): CIF file op0c00416_si_003.cif (crystal structure) (license: CC BY-NC 4.0 as labelled on the ACS figshare mirror)\n- [https://doi.org/10.1021/acs.oprd.0c00416](https://doi.org/10.1021/acs.oprd.0c00416): Article (OPRD 2020) with main-text screening tables and figures (license: closed (ACS))\n\n## Pitfalls\n\nOutcomes are LCAP (area %), not isolated yields. Values come from labelled bar charts. Ru metathesis catalysts are named by vendor codes and need SMILES for organometallic complexes, which may be imperfect. Substrates are large, stereochemically complex intermediates. Some screening conditions (loading, concentration in L/kg, temperature) are described generically and must be matched to each chart. Kinetic monitoring data, if in the main text, are figures.\n\n## Deliver\n\n- `dataset`: the ORD Dataset, compressed (`.binpb.gz`, `.pb.gz`, `.txtpb.gz`, `.pbtxt.gz` or `.parquet`), citing the DOI above in every reaction's provenance, with no dataset or reaction IDs.\n- `sources`: a `.zip` with a `README.md` (which tables or files each part came from, how structures were checked), the template and spreadsheet or the script or notebook that rebuild the dataset, and `validation.txt`, the output of ORD's validator (ord-schema 0.8.3) on the `dataset` file.\n\n## Before you start\n\nOpen the wishlist card. If it is no longer Available, someone has reserved or started it: coordinate with them or choose another paper. Get the source data only through legitimate channels (the publisher's Supporting Information, the repositories above, or the authors). Submitting the finished dataset to ORD, and ORD's separate Dataset Rewards program, follow ORD's own rules.\n","context_md":null,"benchmark":null,"verifier_contract_id":"vct_4t6ri8zibj","verifier_input_bindings":[{"key":"card","content_hash":"sha256:5aba410b4e77da7da53372cdfa4f6215cee43ebb46ad30c2566232129f4de983","size_bytes":4226,"media_type":"application/json","filename":"card.json"}],"skill_refs":[{"skill_version_id":"skv_k5sivlohu1","requirement":"required"}],"changelog_md":null,"created_by_user_id":"usr_llep2e937g","created_at":"2026-09-25T19:27:21Z","sealing":null}}