[1,1'-biphenyl]-4-carbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】28446

【品名】[1,1'-biphenyl]-4-carbaldehyde

【CA登记号】3218-36-8

【分子式】C₁₃H₁₀O

【分子量】182.2218

【元素组成】C 85.69% H 5.53% O 8.78%

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：(X)

In an alternative procedure, condensation of 4-biphenylcarbaldehyde (X) with tert-butyl carbazate afforded hydrazone (XI), which was reduced to the benzylhydrazine (XII) by hydrogenation over Pd/C. Opening of the Boc-protected epoxide (XIII) with hydrazine (XII) gave hydrazinoalcohol (VI). This was deprotected with HCl and then coupled as above with N-methoxycarbonyl-L-tert-leucine (X) by means of TPTU.

参考文献中间体

合成目标

【1】 New aza-dipeptide analogues as potent and orally a. J Med Chem 1998, 41, 18, 3387.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	28443	tert-butyl 2-([1,1'-biphenyl]-4-ylmethyl)-2-[(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl]-1-hydrazinecarboxylate		C₃₃H₄₃N₃O₅	详情	详情
(IX)	23447	(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutyric acid		C₈H₁₅NO₄	详情	详情
(X)	28446	[1,1'-biphenyl]-4-carbaldehyde	3218-36-8	C₁₃H₁₀O	详情	详情
(XI)	28447	tert-butyl (Z)-2-([1,1'-biphenyl]-4-ylmethyl)-1-diazenecarboxylate		C₁₈H₂₀N₂O₂	详情	详情
(XII)	28448	tert-butyl 2-([1,1'-biphenyl]-4-ylmethyl)-1-hydrazinecarboxylate		C₁₈H₂₂N₂O₂	详情	详情
(XIII)	23444	tert-butyl (1S)-1-[(2R)oxiranyl]-2-phenylethylcarbamate		C₁₅H₂₁NO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The reaction of N-(tert-butoxycarbonyl)-L-alanine (I) with biphenyl-4-carbaldehyde (II) by means of oxalyl chloride and ZnCl2 or TsOH gives the oxazolidinone (III), which is alkylated with 4-bromobenzyl bromide (IV) and LHMDS in THF, yielding the alkylated compound (V). The opening of the oxazolidinone ring of (V) with LiOMe and NaHSO3 affords the aminopropionic ester (VI), which is cyclized again with 3,5-dichloroaniline (VII) by means of NaOMe in refluxing toluene to provide imidazolidinedione (VIII). Finally, this compound is methylated with MeI, NaOH and tetrabutylammonium bisulfate to give the target compound.

参考文献中间体

合成目标

【1】 Farina, V.; Napolitano, E.; Crystallization-induced asymmetric transformations and self-regeneration of stereocenters (SROSC): Enantiospecific synthesis of alpha-benzylalanine and hydantoin BIRT-377. Tetrahedron Lett 2001, 42, 18, 3231.

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)	26450	Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid	15761-38-3	C₈H₁₅NO₄	详情	详情
(II)	28446	[1,1'-biphenyl]-4-carbaldehyde	3218-36-8	C₁₃H₁₀O	详情	详情
(III)	47938	tert-butyl (2S,4S)-2-[1,1'-biphenyl]-4-yl-4-methyl-5-oxo-1,3-oxazolidine-3-carboxylate		C₂₁H₂₃NO₄	详情	详情
(IV)	16109	1-bromo-4-(bromomethyl)benzene; 4-Bromobenzyl bromide	589-15-1	C₇H₆Br₂	详情	详情
(V)	47939	tert-butyl (2S,4S)-2-[1,1'-biphenyl]-4-yl-4-(4-bromobenzyl)-4-methyl-5-oxo-1,3-oxazolidine-3-carboxylate		C₂₈H₂₈BrNO₄	详情	详情
(VI)	47940	methyl (2S)-3-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]-2-methylpropanoate		C₁₆H₂₂BrNO₄	详情	详情
(VII)	26542	3,5-dichloroaniline	626-43-7	C₆H₅Cl₂N	详情	详情
(VIII)	47933	(5R)-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-5-methyl-2,4-imidazolidinedione		C₁₇H₁₃BrCl₂N₂O₂	详情	详情

Extended Information