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【结 构 式】

【分子编号】20163

【品名】N-(cyclopentylmethyl)-4-methoxy-N-[(2R)oxiranylmethyl]benzenesulfonamide

【CA登记号】

【 分 子 式 】C16H23NO4S

【 分 子 量 】325.42896

【元素组成】C 59.05% H 7.12% N 4.3% O 19.67% S 9.85%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VII)

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.

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

合成路线2

该中间体在本合成路线中的序号:(VII)

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.

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) 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