• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】10265

【品名】tert-butyl N-[(E)-7-[(2,5-dioxo-1-pyrrolidinyl)oxy]-7-oxo-3-heptenyl]carbamate

【CA登记号】

【 分 子 式 】C16H24N2O6

【 分 子 量 】340.37644

【元素组成】C 56.46% H 7.11% N 8.23% O 28.2%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

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
Extended Information