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【结 构 式】

【分子编号】49445

【品名】ethyl (3R,4R,5S)-4-(acetamido)-5-(allylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

【CA登记号】

【 分 子 式 】C19H32N2O4

【 分 子 量 】352.47416

【元素组成】C 64.74% H 9.15% N 7.95% O 18.16%

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:(IX)

A new synthesis of oseltamivir phosphate has been described: The opening of the oxirane ring of the already reported oseltamivir intermediate (I) by reaction with allylamine (II) in t-BuOMe/MeCN 9:1 provides the allylamino derivative (III), which is deallylated with Pd/C and ethanolamine to give the primary amine (IV). The direct conversion of the amino alcohol (IV) into the vicinal diamine (VIII) is achieved, without isolation of the intermediates, by reaction of compound (IV) with benzaldehyde to give the benzaldehyde imine (V), mesylation of (V) with MsCl and TEA to the mesylate (VI) and treatment of (VI) with allylamine (II) to yield the aziridine intermediate (VII) that opens to the vicinal diamine (VIII). Acylation of the primary amino group of (VIII) with acetic anhydride in acetic acid provides the acetamide (IX), which is finally deallylated with Pd/C and ethanolamine as before and treated with H3PO4.

1 Trussardi, R.; Karpf, M.; New, azide-free transformation of epoxides into 1,2-diamino compounds: Synthesis of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu). J Org Chem 2001, 66, 6, 2044.
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) 29902 ethyl (1S,5R,6S)-5-(1-ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate C14H22O4 详情 详情
(II) 13672 Allylamine; 2-Propen-1-amine 107-11-9 C3H7N 详情 详情
(III) 49440 ethyl (3R,4S,5R)-5-(allylamino)-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate C17H29NO4 详情 详情
(IV) 49441 ethyl (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate C14H25NO4 详情 详情
(V) 49444 ethyl (3R,4R,5S)-5-(allylamino)-4-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate C17H30N2O3 详情 详情
(VI) 49443 ethyl (3R,4S,5R)-3-(1-ethylpropoxy)-4-[(methylsulfonyl)oxy]-5-[[(Z)-benzylidene]amino]-1-cyclohexene-1-carboxylate C22H31NO6S 详情 详情
(VII) 29904 ethyl (1R,5R,6R)-5-(1-ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate C14H23NO3 详情 详情
(VIII) 49444 ethyl (3R,4R,5S)-5-(allylamino)-4-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate C17H30N2O3 详情 详情
(IX) 49445 ethyl (3R,4R,5S)-4-(acetamido)-5-(allylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate C19H32N2O4 详情 详情
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