methyl 1-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropyl)amino]cyclohexanecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】20166

【品名】methyl 1-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropyl)amino]cyclohexanecarboxylate

【CA登记号】

【分子式】C₂₅H₃₂N₂O₄

【分子量】424.54016

【元素组成】C 70.73% H 7.6% N 6.6% O 15.07%

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：(III)

Reductive alkylation of aminoester (I) with N-Cbz-L-phenylalaninal (II) using NaBH3CN and AcOH in DMF provided compound (III). Subsequent deprotection of the Cbz group of (III) with HBr in AcOH afforded the diamine salt (IV), which upon basification with diisopropylamine resulted in lactamization to produce piperazinone (V). The secondary amine of (V) was then protected by alkylation with benzyl bromide to give (VI), which was condensed with the epoxisulfonamide (VII) in the presence of NaH in DMF to furnish (VIII). Finally, hydrogenolysis of the N-benzyl group in the presence of Pd(OH)2 yielded 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	分子式	供应商	用于合成
(I)	20164	methyl 1-aminocyclohexanecarboxylate	C₈H₁₅NO₂	详情	详情
(II)	16586	benzyl N-[(1S)-1-benzyl-2-oxoethyl]carbamate	C₁₇H₁₇NO₃	详情	详情
(III)	20166	methyl 1-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropyl)amino]cyclohexanecarboxylate	C₂₅H₃₂N₂O₄	详情	详情
(IV)	20167	methyl 1-[[(2S)-2-amino-3-phenylpropyl]amino]cyclohexanecarboxylate hydrobromide	C₁₇H₂₇BrN₂O₂	详情	详情
(V)	20168	(3S)-3-benzyl-1,4-diazaspiro[5.5]undecan-5-one	C₁₆H₂₂N₂O	详情	详情
(VI)	20169	(3S)-1,3-dibenzyl-1,4-diazaspiro[5.5]undecan-5-one	C₂₃H₂₈N₂O	详情	详情
(VII)	20163	N-(cyclopentylmethyl)-4-methoxy-N-[(2R)oxiranylmethyl]benzenesulfonamide	C₁₆H₂₃NO₄S	详情	详情
(VIII)	20171	N-(cyclopentylmethyl)-N-[(2S)-3-[(3S)-1,3-dibenzyl-5-oxo-1,4-diazaspiro[5.5]undec-4-yl]-2-hydroxypropyl]-4-methoxybenzenesulfonamide	C₃₉H₅₁N₃O₅S	详情	详情

Extended Information