{
  "source": "ORD Dataset Wishlist",
  "snapshot_date": "2026-09-25",
  "ord_wishlist_status_at_snapshot": "Available",
  "ord_wishlist_card": "https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570074",
  "ord_data_issue": null,
  "title": "Accelerated Development of a Scalable Ring-Closing Metathesis to Manufacture AMG 176 Using a Combined High-Throughput Experimentation and Computational Modeling Approach",
  "doi": "10.1021/acs.oprd.0c00416",
  "journal": "OPRD",
  "publication_date": "2020-11-25",
  "authors": [
    "Gabrielle St‐Pierre",
    "Alan H. Cherney",
    "Wencan Chen",
    "Xiaofei Dong",
    "Peter K. Dornan",
    "Daniel J. Griffin",
    "Kendall N. Houk",
    "Janice B. Lin",
    "Stephen A. Osgood",
    "Maria Victoria Silva Elipe",
    "Heath C. Timmons",
    "Yong Xie"
  ],
  "article_open_access": {
    "status": "closed",
    "license": null
  },
  "dataset_size_estimate": null,
  "experiment_type": null,
  "ord_priority": null,
  "ord_difficulty": null,
  "source_data_kind": "si_pdf_tables",
  "smiles_in_source": "no",
  "needs_author_contact": false,
  "data_locations": [
    {
      "url": "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",
      "what": "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"
    },
    {
      "url": "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",
      "what": "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"
    },
    {
      "url": "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",
      "what": "CIF file op0c00416_si_003.cif (crystal structure)",
      "license": "CC BY-NC 4.0 as labelled on the ACS figshare mirror"
    },
    {
      "url": "https://doi.org/10.1021/acs.oprd.0c00416",
      "what": "Article (OPRD 2020) with main-text screening tables and figures",
      "license": "closed (ACS)"
    }
  ],
  "notes": "This 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.",
  "verification_caveats": "Outcomes 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."
}