N-omega'-nitro-D-arginine -Drug Synthesis Database

【结构式】

【分子编号】25103

【品名】N-omega'-nitro-D-arginine

【CA登记号】

【分子式】C₆H₁₃N₅O₄

【分子量】219.20052

【元素组成】C 32.88% H 5.98% N 31.95% O 29.2%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The reaction of Nomega'-nitro-D-arginine (I) with 2,2-diphenylacetyl chloride (II) by means of NaOH in THF/water gives the expected Nalpha-diphenylacetyl derivative (III), which is condensed with 4-(ureidomethyl)benzylamine (IV) by means of TBTU and DIEA in THF to yield the corresponding amide (V). Finally, this compound is hydrogenated with H2 over Pd/C in aqueous acetic acid in order to eliminate the Nomega'-nitro group and treated with trifluoroacetic acid to provide the target compound.

参考文献中间体

合成目标

【1】 Engel, W.; Eberlein, W.; Rudolf, K.; Doods, H.; Wieland, H.-A.; Willim, K.-D.; Entzeroth, M.; Wienen, W. (Dr. Karl Thomae GmbH); Amino acid derivs., pharmaceutical compsns. containing these cpds. and processes for preparing them. DE 19544687; EP 0885186; WO 9719911 .

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)	25103	N-omega'-nitro-D-arginine		C₆H₁₃N₅O₄	详情	详情
(II)	23800	Diphenylacetyl chloride; 2,2-diphenylacetyl chloride	1871-76-7	C₁₄H₁₁ClO	详情	详情
(III)	25104	N-alpha-(2,2-diphenylacetyl)-N-omega'-nitro-D-arginine		C₂₀H₂₃N₅O₅	详情	详情
(IV)	25105	N-[4-(aminomethyl)benzyl]urea		C₉H₁₃N₃O	详情	详情
(V)	25106	N-alpha-(2,2-diphenylacetyl)-N-omega'-nitro-N1-[4-(ureidomethyl)benzyl]-D-arginine		C₂₉H₃₄N₈O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XI)

The intermediate 3-(4-cyanobenzyloxy)isoxazole-5-carboxylic acid (VII) has been obtained by condensation of 4-(bromomethyl)benzonitrile (IX) with 3-hydroxyisoxazole-5-carboxylic acid methyl ester (X) by means of K2CO3 in hot DMF to yield the benzyloxy derivative (XI), which is finally hydrolyzed with LiOH in THF to provide the target intermediate (VII).

参考文献中间体

合成目标

【1】 Xue, C.-B.; Roderick, J.; Mousa, S.; Olson, R.E.; DeGrado, W.F.; Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists. Bioorg Med Chem Lett 1998, 8, 24, 3499.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	25098	3-[(4-cyanobenzyl)oxy]-5-isoxazolecarboxylic acid		C₁₂H₈N₂O₄	详情	详情
(IX)	14200	4-(Bromomethyl)benzonitrile; alpha-Bromo-p-tolunitrile	17201-43-3	C₈H₆BrN	详情	详情
(X)	25101	methyl 3-hydroxy-5-isoxazolecarboxylate	10068-07-2	C₅H₅NO₄	详情	详情
(XI)	25103	N-omega'-nitro-D-arginine		C₆H₁₃N₅O₄	详情	详情

Extended Information