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brine","input":{"components":[{"identifiers":[{"type":"SMILES","value":"O"},{"type":"NAME","value":"water"}]},{"identifiers":[{"type":"SMILES","value":"[Na+].[Cl-]"},{"type":"NAME","value":"NaCl"}]}]}},{"type":"DRY_WITH_MATERIAL","details":"dried over MgSO4"},{"type":"CONCENTRATION","details":"concentrated in vacuo"},{"type":"FLASH_CHROMATOGRAPHY","details":"Fluka, 230-400 mesh, solvent system: 10% ethyl acetate/hexane"}],"outcomes":[{"reaction_time":{"value":72,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CC(=O)C1=CC=C(C2CCCCN2C(=O)OC(C)(C)C)C=C1"}],"is_desired_product":true,"measurements":[{"analysis_key":"1h nmr","type":"IDENTITY"},{"analysis_key":"13c 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()"}},"instrument_manufacturer":"Bruker"}}}],"provenance":{"doi":"10.1126/science.1255525","publication_url":"https://science.sciencemag.org/content/345/6195/437"}}},"entities":[{"slug":"ord-compound-31d1d41971f1d21bf47f","name":"Boc-Pip-OH","smiles":"CC(C)(C)OC(=O)N1CCCCC1C(=O)O","inchi":"InChI=1S/C11H19NO4/c1-11(2,3)16-10(15)12-7-5-4-6-8(12)9(13)14/h8H,4-7H2,1-3H3,(H,13,14)","formula":"C11H19NO4"},{"slug":"ord-compound-107a56b73192e42c88c9","name":"1-acetyl-4-bromobenzene","smiles":"CC(=O)c1ccc(Br)cc1","inchi":"InChI=1S/C8H7BrO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,1H3","formula":"C8H7BrO"},{"slug":"ord-compound-243b772bd882288ecee5","name":"C18H25NO3 · ORD ZSYSIHPTMRWZKU-UHFFFAOYSA-N","smiles":"CC(=O)c1ccc(C2CCCCN2C(=O)OC(C)(C)C)cc1","inchi":"InChI=1S/C18H25NO3/c1-13(20)14-8-10-15(11-9-14)16-7-5-6-12-19(16)17(21)22-18(2,3)4/h8-11,16H,5-7,12H2,1-4H3","formula":"C18H25NO3"}],"dataset":{"dataset_id":"ord_dataset-89b083710e2d441aa0040c361d63359f","name":"Coupling of α-carboxyl sp3-carbons with 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Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}