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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: 15% ethyl acetate/hexane"}],"outcomes":[{"reaction_time":{"value":72,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)OC(=O)N1CCCC1c1ccc(Cl)cc1"}],"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-29b570df9f1465a7f98a","name":"Boc-Pro-OH","smiles":"CC(C)(C)OC(=O)N1CCCC1C(=O)O","inchi":"InChI=1S/C10H17NO4/c1-10(2,3)15-9(14)11-6-4-5-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)","formula":"C10H17NO4"},{"slug":"ord-compound-53d28e41f145a973fb61","name":"1-iodo,4-chlorobenzene","smiles":"Clc1ccc(I)cc1","inchi":"InChI=1S/C6H4ClI/c7-5-1-3-6(8)4-2-5/h1-4H","formula":"C6H4ClI"},{"slug":"ord-compound-68cad297e24b2570fc9e","name":"C15H20ClNO2 · ORD MLNBPUVXUSNQNC-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)N1CCCC1c1ccc(Cl)cc1","inchi":"InChI=1S/C15H20ClNO2/c1-15(2,3)19-14(18)17-10-4-5-13(17)11-6-8-12(16)9-7-11/h6-9,13H,4-5,10H2,1-3H3","formula":"C15H20ClNO2"}],"dataset":{"dataset_id":"ord_dataset-89b083710e2d441aa0040c361d63359f","name":"Coupling of α-carboxyl sp3-carbons with aryl 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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"]}