【结 构 式】 |
【分子编号】61464 【品名】2-[sec-butyl(2-chloroacetyl)amino]acetamide 【CA登记号】 |
【 分 子 式 】C8H15ClN2O2 【 分 子 量 】206.67208 【元素组成】C 46.49% H 7.32% Cl 17.15% N 13.55% O 15.48% |
合成路线1
该中间体在本合成路线中的序号:(V)The title compound is prepared by solid phase synthesis employing a Rink amide resin. Acylation of the resin with chloroacetyl chloride (I) affords the chloroacetyl resin (II). Subsequent chloride displacement with s-butylamine (III) provides the aminoacid-bound resin (IV). A new acylation of (IV) with chloroacetyl chloride (I) yields the chloroacetamide (V), which is then displaced by cyclopropylamine (VI), yielding the dipeptide derivative (VII). Then, a further coupling of (VII) with acid chloride (I), followed by displacement of the resultant chloroacetamide resin (VIII) with N-(2-aminoethyl)pyrrolidine (IX) gives rise to the tripeptide resin (X). Finally, cleavage of the dipeptide amide from the solid support is accomplished by treatment with trifluoroacetic acid in CH2Cl2
【1】 Montoliu, C.; et al.; Prevention of in vivo excitotoxicity by a family of trialkylglycines, a novel class of neuroprotectants. J. Pharm. Exp. Ther. 2002, 301, 1, 29. |
【2】 Felipo Orts, V.; Montoliu Felix, C.; Ferrer Montiel, A.; Planells Cases, R.; Merino Fernandez, J.M.; Perez Paya, E.; Sanchez Baeza, F.; Humet, M.; Messeguer Peypoch, A. (DiverDrugs SL); N-Alkylglycine trimeres capable of protecting neurons against excitotoxic aggressions and compsns. containing said trimeres. WO 0228885 . |
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) | 11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 |
(II) | 28964 | 2-chloroacetamide | 79-07-2 | C2H4ClNO | 详情 | 详情 |
(III) | 61462 | sec-butyl amine; 2-Butanamine, (+-)-; 2-Aminobutane; 2-Butylamine; 2-Butanamine; 2-aminobutane base; butafume; deccotane; frucote; Butanamine; Methylpropylamine; SEC-BUTYLAMINE; (+/-)-sec-Butylamine; (+/-)-2-Aminobutane; Sec-Aminobutane; Sec-Butylamine; 2-Aminobutan; (+/-)-2-Butylamine; sec-Butylamine; Butylamine (sec); SBA; METHYL-n-PROPYLAMINE; (+/-)-2-Aminobutane | 13952-84-6 | C4H11N | 详情 | 详情 |
(IV) | 61463 | 2-(sec-butylamino)acetamide | C6H14N2O | 详情 | 详情 | |
(V) | 61464 | 2-[sec-butyl(2-chloroacetyl)amino]acetamide | C8H15ClN2O2 | 详情 | 详情 | |
(VI) | 12263 | Cyclopropylamine; Cyclopropanamine | 765-30-0 | C3H7N | 详情 | 详情 |
(VII) | 61465 | 2-{sec-butyl[2-(cyclopropylamino)acetyl]amino}acetamide | C11H21N3O2 | 详情 | 详情 | |
(VIII) | 61466 | 2-(sec-butyl{2-[(2-chloroacetyl)(cyclopropyl)amino]acetyl}amino)acetamide | C13H22ClN3O3 | 详情 | 详情 | |
(IX) | 18161 | 2-(1-pyrrolidinyl)ethylamine; 2-(1-pyrrolidinyl)-1-ethanamine; 1-Pyrrolidineethanamine | 7154-73-6 | C6H14N2 | 详情 | 详情 |
(X) | 61467 | 2-(sec-butyl{2-[cyclopropyl(2-{[2-(1-pyrrolidinyl)ethyl]amino}acetyl)amino]acetyl}amino)acetamide | C19H35N5O3 | 详情 | 详情 |