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【结 构 式】 
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【分子编号】31970 【品名】4-Hydroxy-17O-phenylalanine; Hydroxy Phenyl Alanine; DL-tyrosine; 2-Amino-3-(4-hydroxyphenyl)propionic acid; 3-(4-Hydroxyphenyl)alanine; beta-(p-Hydroxyphenyl)alanine; tyrosine 【CA登记号】556-03-6 |
【 分 子 式 】C9H11NO3 【 分 子 量 】181.19128 【元素组成】C 59.66% H 6.12% N 7.73% O 26.49% |
合成路线1
该中间体在本合成路线中的序号：(I)The benzoylation of tyrosine (I) with benzoyl chloride (II) in aqueous NaOH gives O,N-(di-benzoyl)-D,L-tyrosine (III), which by reaction with di-n-propylamine (A) by means of ethyl chlorocarbonate and triethylamine in acetone is converted into O,N-(di-benzoyl)-D,L-tyrosyl-di-n-propylamide (IV). Selective hydrolysis of (IV) with NaOH in methanol - water affords N-benzoyl-D,L-tyrosyl-di-n-propylamide (V), which is finally condensed with 2-(diethylamino)ethyl chloride (VI) by means of sodium methoxide in refluxing toluene.
| 【1】 Senin; et al.; Activity of derivatives of tyrosine on gastrointestinal motility. Gastrointestinal Motility in Health and Disease. Duthie, H.L. (Ed.); MTP Press Limited, Lancaster 1978, 417-427. |
| 【2】 Makovec, F.; Rovati, L.; Senini, P. (Rotta Research Laboratorium SpA); O-Tertiary amino-alkyl-N-benzoyl tyrosil amides. DE 2503992; FR 2259592; GB 1467927; JP 50116442; NL 167683C; US 4004008 . |
| 【3】 Serradell, M.N.; de Angelis, L.; Blancafort, P.; Castaner, J.; Tiropramide. Drugs Fut 1982, 7, 6, 413. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 21856 | N,N-dipropylamine; N-propyl-1-propanamine | 142-84-7 | C6H15N | 详情 | 详情 |
| (I) | 31970 | 4-Hydroxy-17O-phenylalanine; Hydroxy Phenyl Alanine; DL-tyrosine; 2-Amino-3-(4-hydroxyphenyl)propionic acid; 3-(4-Hydroxyphenyl)alanine; beta-(p-Hydroxyphenyl)alanine; tyrosine | 556-03-6 | C9H11NO3 | 详情 | 详情 |
| (II) | 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 |
| (III) | 31971 | N-benzoyl-4-(benzoyloxy)phenylalanine | C23H19NO5 | 详情 | 详情 | |
| (IV) | 31972 | 4-[2-(benzoylamino)-3-(dipropylamino)-3-oxopropyl]phenyl benzoate | C29H32N2O4 | 详情 | 详情 | |
| (V) | 31973 | N-[2-(dipropylamino)-1-(4-hydroxybenzyl)-2-oxoethyl]benzamide | C22H28N2O3 | 详情 | 详情 | |
| (VI) | 16194 | 2-chloro-N,N-diethyl-1-ethanamine; N-(2-chloroethyl)-N,N-diethylamine | 100-35-6 | C6H14ClN | 详情 | 详情 |