Mabuterol
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| _other_data=1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(tert-butylamino)ethanol
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| _datapage = Mabuterol (data page) | _vaccine_target=_type_not_vaccine | _legal_all= | _ATC_prefix_supplemental= | _has_EMA_link = | CAS_number=56341-08-3 | PubChem=3995 | ChemSpiderID=3857 | ChEBI=135325 | ChEMBL=86749 | DrugBank= | KEGG= | _hasInChI_or_Key=yes | UNII=R4K19W6S7Q | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =
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Mabuterol is a selective β2 adrenoreceptor agonist.[1][2]
Synthesis
The halogenation of 2-(Trifluoromethyl)aniline [88-17-5] (1) with iodine and sodium bicarbonate resulted in 2-Amino-5-Iodobenzotrifluoride [97760-97-9] (2). Protection with acetic anhydride followed by nucleophilic aromatic displacement with copper(I)cyanide gave N-[4-cyano-2-(trifluoromethyl)phenyl]acetamide [175277-96-0] (3). Hydrolysis of the nitrile and the protecting group gave 4-amino-3-(trifluoromethyl)benzoic acid [400-76-0] (4). Halogenation with chlorine gave 4-Amino-3-Chloro-5-(Trifluoromethyl)Benzoic Acid [95656-52-3] (5). Halogenation of the acid with thionyl chloride gave 4-Amino-3-chloro-5-(trifluoromethyl)benzoylchloride [63498-15-7] (6). Treatment with diethyl malonate [105-53-3] gave the acetophenone and hence 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]ethanone [97760-76-4] (7). Halogenation with bromine in acetic acid led to 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-bromoethanone [97760-87-7] (8). Treatment with tert-butylamine [75-64-9] yielded 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(tert-butylamino)ethenone, CID:13355601 (9). Reduction of the ketone with sodium borohydride completed the synthesis of Mabuterol (10).
See also
- Clenbuterol
- Cimaterol
- Trantinterol (regioisomer)
References
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- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Engelhardt G, Keck J, "Aminophenyl ethanolamines and oxazolidines - having analgesic, uterus spasmolytic and anti-spasmodic activity on cross-striped muscle structure", issued Script error: No such module "auto date formatter"., assigned to Thomae GmbH.Script error: No such module "Check for unknown parameters".
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- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, assigned to Thomae GmbH.Script error: No such module "Check for unknown parameters".
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