(2S)-N(1)-benzyl-3-phenyl-1,2-propanediamine; N-[(2S)-2-amino-3-phenylpropyl]-N-benzylamine -Drug Synthesis Database

【结构式】

【分子编号】20161

【品名】(2S)-N(1)-benzyl-3-phenyl-1,2-propanediamine; N-[(2S)-2-amino-3-phenylpropyl]-N-benzylamine

【CA登记号】

【分子式】C₁₆H₂₀N₂

【分子量】240.34828

【元素组成】C 79.96% H 8.39% N 11.66%

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)

N-Cbz-L-Phenylalaninol (I) was converted to mesylate (II) on treatment with methanesulfonyl chloride and Et3N, and then treated with benzylamine (III) in the presence of NaI to give (IV). Subsequent deprotection of the Cbz group of (IV) with HBr in AcOH afforded diamine (V), which was treated with carbonyl diimidazole to produce the cyclic urea (VI). Finally, condensation with the epoxisulfonamide (VII) in the presence of NaH in DMF provided the target compound.

参考文献中间体

合成目标

【1】 Salituro, F.G.; Baker, C.T.; Court, J.J.; Deininger, D.D.; Kim, E.E.; Li, B.; Novak, P.M.; Rao, B.G.; Pazhanisamy, S.; Porter, M.D.; Schairer, W.C.; Tung, R.D.; Design and synthesis of novel conformationally restricted HIV protease inhibitors. Bioorg Med Chem Lett 1998, 8, 24, 3637.

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)	16585	benzyl N-[(1S)-1-benzyl-2-hydroxyethyl]carbamate		C₁₇H₁₉NO₃	详情	详情
(II)	20158	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropyl methanesulfonate		C₁₈H₂₁NO₅S	详情	详情
(III)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(IV)	20160	benzyl (1S)-1-benzyl-2-(benzylamino)ethylcarbamate		C₂₄H₂₆N₂O₂	详情	详情
(V)	20161	(2S)-N(1)-benzyl-3-phenyl-1,2-propanediamine; N-[(2S)-2-amino-3-phenylpropyl]-N-benzylamine		C₁₆H₂₀N₂	详情	详情
(VI)	20162	(4S)-1,4-dibenzyl-2-imidazolidinone		C₁₇H₁₈N₂O	详情	详情
(VII)	20163	N-(cyclopentylmethyl)-4-methoxy-N-[(2R)oxiranylmethyl]benzenesulfonamide		C₁₆H₂₃NO₄S	详情	详情

Extended Information