{"doi":"10.1139/v71-317","title":"Synthesis of <i>N</i>-Methylamino Acid Derivatives from Amino Acid Derivatives using Sodium Hydride/Methyl Iodide","abstract":"<jats:p> Reaction of N-acetyl-, N-benzoyl-, and N-carbobenzoxy derivatives of aliphatic amino acids with sodium hydride/methyl iodide in tetrahydrofuran containing dimethylformamide at 80° gave the corresponding N-methylamino acid methyl esters as oils in high yields. Saponification of these gave the N-protected-N-methylamino acids, and decarbobenzoxylation gave the N-methylamino acid methyl ester hydrobomides. The products are essentially optically pure and free of unmethylated amino acid derivative. </jats:p>","journal":"Canadian Journal of Chemistry","year":1971,"id":21901,"datarank":6.998255185168994,"base_score":4.174387269895637,"endowment":4.174387269895637,"self_citation_contribution":0.6261580904843456,"citation_network_contribution":6.372097094684649,"self_endowment_contribution":0.6261580904843456,"citer_contribution":6.372097094684649,"corpus_percentile":null,"corpus_rank":null,"citation_count":64,"citer_count":59,"citers_with_citation_signal":56,"citers_with_endowment":56,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":139390,"name":"N. Leo Benoiton","orcid":null,"position":1,"is_corresponding":false},{"id":139388,"name":"John R. Coggins","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":4.174387269895637,"endowment":4.174387269895637,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"21071399","pmcid":null,"openalex_id":"https://openalex.org/W2091775418","authors":[],"funders":[],"total_grants":0,"fwci":1.1948,"citation_percentile":0.78071349,"influential_citations":0,"citation_trend":[{"year":2014,"count":1},{"year":2015,"count":1},{"year":2022,"count":1},{"year":2024,"count":1},{"year":2026,"count":1}],"oa_status":"bronze","license":"http://www.nrcresearchpress.com/page/about/CorporateTextAndDataMining","oa_locations":[{"url":"https://cdnsciencepub.com/doi/pdf/10.1139/v71-317","host_type":"journal"},{"url":"https://cdnsciencepub.com/doi/pdf/10.1139/v71-317","host_type":"BRONZE"},{"url":"https://cdnsciencepub.com/doi/pdf/10.1139/v71-317","host_type":"publisher"},{"url":"https://doi.org/10.1139/v71-317","host_type":"journal"}],"fields_of_study":["Chemical Synthesis and Analysis","Synthetic Organic Chemistry Methods","Asymmetric Synthesis and Catalysis","Chemistry"],"mesh_terms":[],"keywords":["Chemistry","Sodium hydride","Methyl iodide","Tetrahydrofuran","Saponification","Sodium iodide","Hydride","Organic chemistry","Dimethylformamide","Iodide","Sodium","Derivative (finance)","Amino acid","Medicinal chemistry"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-06T17:10:59.967413Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}