【结 构 式】 |
【分子编号】10261 【品名】tert-butyl N-(3-oxopropyl)carbamate 【CA登记号】 |
【 分 子 式 】C8H15NO3 【 分 子 量 】173.21204 【元素组成】C 55.47% H 8.73% N 8.09% O 27.71% |
合成路线1
该中间体在本合成路线中的序号:(II)The synthesis of racemic 15-deoxyspergualin and tritium-labeled compound has been described: The oxidation of N-(3-hydroxypropyl)carbamic acid tert-butyl ester (I) with pyridinium chlorochromate in dichloromethane gives N-(3-oxopropyl)carbamic acid tert-butyl ester (II), which is condensed with 4-(triphenylphosphonium)butyrate (III) by means of lithium bis(trimethylsilyl)amide in THF yielding 7-(tert-butoxycarbonylamino)-4-heptenoic acid (IV). The esterification of (IV) with N-hydroxysuccinimide (V) by means of dicyclohexylcarbodiimide and 1-hydroxybenzotriazole affords the corresponding ester (VI), which is treated with ammonia in methanol giving the corresponding amide (VII). The hydrolysis of (VII) with HCl in ethyl acetate yields 7-amino-4-heptenamide (VIII), which is treated with 3,5-dimethylpyrazole-1-carboxamidine (IX) and K2CO3 in methanol affording 7-guanidino-4-heptenamide (X). The reduction of (X) gives 7-guanidinoheptanamide (XI), which is finally condensed with glyoxylspermidine (XII) by means of glutaric acid in hot water. The tritium-labeled compound can also be obtained in the same way by performing the reduction of heptenamide (X) with tritium gas.
【1】 Cook, D.J.; Tepper, M.A.; Saulnier, M.G.; Dischino, D.D.; Synthesis of tritium labeled (±) 15-deoxyspergualin trihydrochloride. J Label Compd Radiopharm 1993, 33, 2, 137. |
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) | 10260 | tert-butyl N-(3-hydroxypropyl)carbamate | 58885-58-8 | C8H17NO3 | 详情 | 详情 |
(II) | 10261 | tert-butyl N-(3-oxopropyl)carbamate | C8H15NO3 | 详情 | 详情 | |
(III) | 10262 | 4-(triphenylphosphonio)butanoate | C22H22O2P | 详情 | 详情 | |
(IV) | 10263 | (E)-7-[(tert-Butoxycarbonyl)amino]-4-heptenoic acid | C12H21NO4 | 详情 | 详情 | |
(V) | 10264 | 1-Hydroxydihydro-1H-pyrrole-2,5-dione; N-Hydroxysuccinimide; 1-Hydroxy-2,5-pyrrolidinedione | 6066-82-6 | C4H5NO3 | 详情 | 详情 |
(VI) | 10265 | tert-butyl N-[(E)-7-[(2,5-dioxo-1-pyrrolidinyl)oxy]-7-oxo-3-heptenyl]carbamate | C16H24N2O6 | 详情 | 详情 | |
(VII) | 10266 | tert-butyl N-[(E)-7-amino-7-oxo-3-heptenyl]carbamate | C12H22N2O3 | 详情 | 详情 | |
(VIII) | 10267 | (E)-7-Amino-4-heptenamide | C7H14N2O | 详情 | 详情 | |
(IX) | 10268 | 3,5-Dimethyl-1H-pyrazole-1-carboximidamide | C6H10N4 | 详情 | 详情 | |
(X) | 10269 | (E)-7-[[Amino(imino)methyl]amino]-4-heptenamide | C8H16N4O | 详情 | 详情 | |
(XI) | 10270 | 7-[[Amino(imino)methyl]amino]heptanamide | C8H18N4O | 详情 | 详情 | |
(XI) | 44635 | 7-[[amino(imino)methyl]amino]heptanamide | C8H18N4O | 详情 | 详情 | |
(XII) | 10271 | N-[4-[(3-Aminopropyl)amino]butyl]-2,2-dihydroxyacetamide | C9H21N3O3 | 详情 | 详情 |