-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】2-(Acetoxymethyl)-4(S)-[2-[5-(benzyloxycarbonylamino)-6-oxo-2-phenyl-1,6-dihydropyrimidin-1-yl]acetamido]-2-pentenoic acid methyl ester
　　　　　　N-[1-[N-[3-(Acetoxymethyl)-4-methoxy-1(S)-methyl-4-oxo-2-butenyl]carbamoylmethyl]-6-oxo-2-phenyl-1,6-dihydropyrimidin-5-yl]carbamic acid benzyl ester

【CA登记号】

【分子式】C₂₉H₃₀N₄O₈

【分子量】562.58445

【开发单位】Walter Reed Army Institute (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Treatment of Protozoal Diseases

合成路线1 合成路线2

合成路线1

The Baylis-Hillman reaction between N-Boc-alaninal (I) and methyl acrylate (II) in the presence of DABCO yields the allylic alcohol adduct (III). Subsequent Mitsunobu coupling with acetic acid leads to the rearranged allylic acetate (IV). Acidic Boc group cleavage in (IV) then gives the amino ester intermediate (V).

参考文献中间体

【1】 Zhu, S.; et al.; Synthesis and in vitro studies of novel pyrimidinyl peptidomimetics as potential antimalarial therapeutic agents. J Med Chem 2002, 45, 16, 3491.

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)	59029	tert-butyl (1S)-1-methyl-2-oxoethylcarbamate		C₈H₁₅NO₃	详情	详情
(II)	14156	methyl acrylate	96-33-3	C₄H₆O₂	详情	详情
(III)	59026	methyl 2-{(2S)-2-[(tert-butoxycarbonyl)amino]-1-hydroxypropyl}acrylate		C₁₂H₂₁NO₅	详情	详情
(IV)	59027	methyl (E,4S)-2-[(acetyloxy)methyl]-4-[(tert-butoxycarbonyl)amino]-2-pentenoate		C₁₄H₂₃NO₆	详情	详情
(V)	59028	methyl (E,4S)-2-[(acetyloxy)methyl]-4-amino-2-pentenoate		C₉H₁₅NO₄	详情	详情

合成路线2

The pyrimidinone acetaldehyde (VI) is oxidized to the corresponding acid (VII) by means of sodium chlorite. Then, coupling of acid (VII) with amino ester (V) using DCC and HOBt provides the target amide.

参考文献中间体

【1】 Zhu, S.; et al.; Synthesis and in vitro studies of novel pyrimidinyl peptidomimetics as potential antimalarial therapeutic agents. J Med Chem 2002, 45, 16, 3491.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(V)	59028	methyl (E,4S)-2-[(acetyloxy)methyl]-4-amino-2-pentenoate	C₉H₁₅NO₄	详情	详情
(VI)	51965	benzyl 6-oxo-1-(2-oxoethyl)-2-phenyl-1,6-dihydro-5-pyrimidinylcarbamate	C₂₀H₁₇N₃O₄	详情	详情
(VII)	47808	2-[5-[[(benzyloxy)carbonyl]amino]-6-oxo-2-phenyl-1(6H)-pyrimidinyl]acetic acid	C₂₀H₁₇N₃O₅	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)