(3R)-1-(4-fluorobenzyl)-3-methyl-2,5-piperazinedione -Drug Synthesis Database

【结构式】

【分子编号】61039

【品名】(3R)-1-(4-fluorobenzyl)-3-methyl-2,5-piperazinedione

【CA登记号】

【分子式】C₁₂H₁₃FN₂O₂

【分子量】236.2459032

【元素组成】C 61.01% H 5.55% F 8.04% N 11.86% O 13.54%

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：(V)

In an alternative procedure, N-Boc-D-alanine (I) is activated as the mixed anhydride (II) by treatment with isobutyl chloroformate. Coupling of anhydride (II) with N-(4-fluorobenzyl)glycine methyl ester (III) produces dipeptide (IV). Further cleavage of the N-Boc protecting group of (IV) under acidic conditions proceeds with concomitant cyclization to the diketopiperazine (V). This is then reduced by means of LiAlH4 to piperazine (VI). Finally, acylation of piperazine (VI) with (4-chlorophenoxy)acetyl chloride (VII) provides the title compound.

参考文献中间体

合成目标

【1】 Islam, I.; May, K.; Bauman, J.; et al.; Synthesis and SAR of CCR1-specific non-peptide antagonists. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 334.

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)	15859	Boc-D-Alanine; (2R)-2-[(tert-butoxycarbonyl)amino]propionic acid	7764-95-6	C₈H₁₅NO₄	详情	详情
(II)	61036	®-2-((tert-butoxycarbonyl)amino)propanoic (isobutyl carbonic) anhydride		C₁₃H₂₃NO₆	详情	详情
(III)	61037	methyl 2-[(4-fluorobenzyl)amino]acetate		C₁₀H₁₂FNO₂	详情	详情
(IV)	61038	methyl 2-[{(2R)-2-[(tert-butoxycarbonyl)amino]propanoyl}(4-fluorobenzyl)amino]acetate		C₁₈H₂₅FN₂O₅	详情	详情
(V)	61039	(3R)-1-(4-fluorobenzyl)-3-methyl-2,5-piperazinedione		C₁₂H₁₃FN₂O₂	详情	详情
(VI)	61035	(3R)-1-(4-fluorobenzyl)-3-methylpiperazine		C₁₂H₁₇FN₂	详情	详情
(VII)	24258	2-(4-chlorophenoxy)acetyl chloride	4122-68-3	C₈H₆Cl₂O₂	详情	详情

Extended Information