methyl 2-([(2R)-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]-2-[(benzylsulfonyl)amino]propanoyl]amino)acetate -Drug Synthesis Database

【结构式】

【分子编号】51049

【品名】methyl 2-([(2R)-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]-2-[(benzylsulfonyl)amino]propanoyl]amino)acetate

【CA登记号】

【分子式】C₃₅H₄₁N₅O₉S

【分子量】707.80484

【元素组成】C 59.39% H 5.84% N 9.89% O 20.34% S 4.53%

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：(VIII)

Coupling of N-Boc-D-pyridylalanine (I) to glycine methyl ester (II) produced the protected dipeptide (III). Subsequent catalytic hydrogenation of the pyridine ring of (III) over PtO2 gave piperidine (IV), which was then treated with the guanylating reagent (V) to afford the guanidine derivative (VI). Acid cleavage of the Boc protecting group of (VI) provided amine (VII). This was condensed with benzylsulfonyl chloride to give sulfonamide (VIII). After basic hydrolysis of the methyl ester of (VIII), the resultant carboxylic acid (IX) was coupled to nitroargininal ethyl aminal (X), yielding amide (XI).

参考文献中间体

合成目标

【1】 Levy, O.E.; Uong, T.H.; Tamura, S.Y.; et al.; Guanylpiperidine peptidomimetics: Potent and selective bis-cation inhibitors of factor Xa. Bioorg Med Chem Lett 2000, 10, 8, 745.

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)	51044	Boc-D-4-Pyridylalanine; Boc-D-4-Pyridylala	37535-58-3	C₁₃H₁₈N₂O₄	详情	详情
(II)	17568	methyl 2-aminoacetate		C₃H₇NO₂	详情	详情
(III)	51045	methyl 2-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-pyridinyl)propanoyl]amino]acetate		C₁₆H₂₃N₃O₅	详情	详情
(IV)	51046	methyl 2-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-piperidinyl)propanoyl]amino]acetate		C₁₆H₂₉N₃O₅	详情	详情
(V)	32861	benzyl (E)-[[(benzyloxy)carbonyl]amino](methylsulfanyl)methylidenecarbamate		C₁₈H₁₈N₂O₄S	详情	详情
(VI)	51047	methyl 2-([(2R)-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)acetate		C₃₃H₄₃N₅O₉	详情	详情
(VII)	51048	methyl 2-([(2R)-2-amino-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]propanoyl]amino)acetate		C₂₈H₃₅N₅O₇	详情	详情
(VIII)	51049	methyl 2-([(2R)-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]-2-[(benzylsulfonyl)amino]propanoyl]amino)acetate		C₃₅H₄₁N₅O₉S	详情	详情
(IX)	51050	2-([(2R)-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]-2-[(benzylsulfonyl)amino]propanoyl]amino)acetic acid		C₃₄H₃₉N₅O₉S	详情	详情
(X)	29388	3(S)-Amino-2-ethoxy-N2-nitropiperidine-1-carboxamidine		C₈H₁₇N₅O₃	详情	详情
(XI)	51051			C₄₂H₅₄N₁₀O₁₁S	详情	详情

Extended Information