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【结 构 式】

【分子编号】19520

【品名】4-[(E)-1-ethyl-4-methoxy-3-butenyl]benzoate

【CA登记号】

【 分 子 式 】C14H17O3

【 分 子 量 】233.28718

【元素组成】C 72.08% H 7.35% O 20.57%

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:(III)

The synthesis of 10-EDAM is as follows: 3-Methoxyallyl chloride (II) is prepared in situ by treatment of 1-methoxyallene (I) with an equivalent of HCl in ether at low temperature. The dianion of p-n-propylbenzoic acid is generated in THF at 0-5 C by lithium diisopropyl amide and subsequently alkylated with (II). The resulting 4-(p-carboxyphenyl)-1-methoxy-1-hexene (III) is brominated at pH 7-8 to give the alpha-bromoaldehyde acid (IV). Condensation with tetraaminopyrimidine in aqueous AcOH and subsequent in situ oxidation of the resultant dihydropteridine affords crystalline 10-ethyl-10-deaza-4-amino-4-desoxypteroic acid (V). Coupling of (V) with diethyl L-glutamate via the mixed anhydride method using isobutyl chloroformate affords the diethyl ester of 10-EDAM (VI). Following chromatographic purification on silica gel, the diester is saponified with 1N NaOH in methoxyethanol at room temperature to yield 10-EDAM.

1 DeGraw, J.I.; EDATREXATE. Drugs Fut 1989, 14, 9, 849.
2 Hoff, S.; Brandsma, L.; Acid catalyzed ring closure of 1-methoxy or 1-(methylthio)-1-(alpha or beta-hydroxyalkyl)allenes. Recl Trav Chim Pays-Bas 1969, 88, 845.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(Va) 11012 4-[1-[(2,4-Diamino-6-pteridinyl)methyl]propyl]benzoic acid C17H18N6O2 详情 详情
(Vb) 13423 1-[(Chlorocarbonyl)oxy]-2-methylpropane; Isobutyl chloroformate;isobutyl carbonochloridate 543-27-1 C5H9ClO2 详情 详情
(IIa) 19518 (E)-3-chloro-1-propenyl methyl ether; (E)-3-chloro-1-methoxy-1-propene C4H7ClO 详情 详情
(IIb) 19519 4-propylbenzoic acid 2438-05-3 C10H12O2 详情 详情
(IVa) 19521 4-(3-bromo-1-ethyl-4-oxobutyl)benzoic acid C13H15BrO3 详情 详情
(IVb) 19522 2,4,6-triamino-5-pyrimidinylamine; 2,4,5,6-pyrimidinetetramine 1004-74-6 C4H8N6 详情 详情
(Vc) 19525 diethyl 2-aminopentanedioate C9H17NO4 详情 详情
(I) 19517 methyl 1,2-propadienyl ether; 1-methoxyallene C4H6O 详情 详情
(III) 19520 4-[(E)-1-ethyl-4-methoxy-3-butenyl]benzoate C14H17O3 详情 详情
(VI) 19526 diethyl 2-[(4-[1-[(2,4-diamino-6-pteridinyl)methyl]propyl]benzoyl)amino]pentanedioate C26H33N7O5 详情 详情
Extended Information