【结 构 式】 |
【分子编号】26635 【品名】benzyl (2S)-2-[[(4-oxobutyl)amino]carbonyl]-1-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C17H22N2O4 【 分 子 量 】318.37276 【元素组成】C 64.13% H 6.97% N 8.8% O 20.1% |
合成路线1
该中间体在本合成路线中的序号:(II)The cyclocondensation of triphenylphosphite (I) with 4-(benzyloxycarbonyl-L-prolylamino)butyraldehyde (II) in hot acetic acid gives the pyrrolidinylphosphonate (III), which is deprotected by hydrogenation with H2 over Pd/C in methanol. The intermediates (I) and (II) have been obtained as follows: Phosphite (I): The acylation of 4-aminophenol (IV) with acetic acid and isobutyl chloroformate in DMF gives N-(4-hydroxyphenyl)acetamide (V), which is allowed to react with PCl3 and triethylamine in DMF yielding phosphite (I). 4-(Benzyloxycarbonyl-L-prolylamino)butyraldehyde (II): The condensation of N-(benzyloxycarbonyl)-L-proline (VI) with 4-aminobutyraldehyde diethylacetal (VII) by means of isobutyl chloroformate and triethylamine in chloroform gives 4-[N-(benzyloxycarbonyl)-L-prolylamino]butyraldehyde diethylacetal (VIII), which is hydrolyzed to the target aldehyde (II) with HCl in THF.
【1】 De Meester, I.; Augustyns, K.; Haemers, A.; Zhang, X.; Vedernikova, I.; Belyaev, A.; Scharpé, S.; Lambeir, A.-M.; Structure-activity relationship of diaryl phosphonate esters as potent irreversible dipeptidyl peptidase IV inhibitors. J Med Chem 1999, 42, 6, 1041. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 26634 | tris[4-(acetamido)phenyl] phosphite | C24H24N3O6P | 详情 | 详情 | |
(II) | 26635 | benzyl (2S)-2-[[(4-oxobutyl)amino]carbonyl]-1-pyrrolidinecarboxylate | C17H22N2O4 | 详情 | 详情 | |
(III) | 26636 | benzyl (2S)-2-[(2-[bis[4-(acetamido)phenoxy]phosphoryl]-1-pyrrolidinyl)carbonyl]-1-pyrrolidinecarboxylate | C33H37N4O8P | 详情 | 详情 | |
(IV) | 15715 | 4-Aminophenol | 123-30-8 | C6H7NO | 详情 | 详情 |
(V) | 21611 | 4'-Hydroxyacetanilide;4-Acetamidophenol;N-Acetyl-4-aminophenol;Paracetamol;Acetaminophen;p-Hydroxyacetanilide; Paracetamol; N-(4-hydroxyphenyl)acetamide | 103-90-2 | C8H9NO2 | 详情 | 详情 |
(VI) | 17005 | (2R)-1-[(benzyloxy)carbonyl]tetrahydro-1H-pyrrole-2-carboxylic acid | C13H15NO4 | 详情 | 详情 | |
(VII) | 23323 | 4,4-diethoxybutylamine; 4,4-diethoxy-1-butanamine | 6346-09-4 | C8H19NO2 | 详情 | 详情 |
(VIII) | 26637 | benzyl (2S)-2-[[(4,4-diethoxybutyl)amino]carbonyl]-1-pyrrolidinecarboxylate | C21H32N2O5 | 详情 | 详情 |