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【结 构 式】

【分子编号】43408

【品名】tert-butyl 4-aminocyclohexylcarbamate

【CA登记号】

【 分 子 式 】C11H22N2O2

【 分 子 量 】214.30796

【元素组成】C 61.65% H 10.35% N 13.07% O 14.93%

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:(XI)

D,L-Glutamic acid (I) was sequentially protected as the gamma-allyl ester (III), upon treatment with allyl alcohol (II) and chlorotrimethylsilane, followed by conversion to the trichloroethyl carbamate (V) by means of chloroformate (IV), and then reaction of (V) with benzyl bromide to afford the alpha-benzyl ester (VI). Deprotection of the trichloroethyl carbamate of (VI) by treatment with zinc dust and HOAc and subsequent condensation of the resulting amine with decanoyl chloride (VII) furnished amide (VIII). The allyl ester of (VIII) was then selectively cleaved by using tetrakistriphenylphosphine palladium(0) and morpholine to give carboxylic acid (IX). trans-1,4-Diaminocyclohexane (X) was protected as the mono tert-butyl carbamate (XI) and then coupled with acid (IX) in the presence of diethylphosphoryl cyanide to yield amide (XII). After acidic Boc cleavage of (XII), coupling of the resulting amine with 2,5-diphenyloxazole-4-carboxylic acid (XIII) by means of bromo-tris(pyrrolidino)phosphonium hexafluorophosphate (PyBroP) afforded (XIV). Finally, hydrolysis of the benzyl ester of (XIV) with LiOH provided the corresponding carboxylic acid.

1 Ducruet, A.P.; Yokokawa, F.; Rice, R.L.; tamura, K.; Lazo, J.S.; Wipf, P.; Yokokama, S.; Identification of new Cdc25 dual specificity phosphatase inhibitors in a targeted small molecule array. Bioorg Med Chem 2000, 8, 6, 1451.
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) 28752 DL-2-Amino propane dicarboxylic acid; DL-2-Aminopentanoic acid; glutamic acid; DL-glutamic acid; (+/-)-2-Aminoglutaric acid 617-65-2 C5H9NO4 详情 详情
(II) 12234 2-Propen-1-ol; Allyl alcohol 107-18-6 C3H6O 详情 详情
(III) 43406 5-(allyloxy)-5-oxonorvaline C8H13NO4 详情 详情
(IV) 13664 1,1,1-Trichloro-2-[(chlorocarbonyl)oxy]ethane; 2,2,2-Trichloroethyl chloroformate 17341-93-4 C3H2Cl4O2 详情 详情
(V) 43399 5-(allyloxy)-5-oxo-N-[(2,2,2-trichloroethoxy)carbonyl]norvaline C11H14Cl3NO6 详情 详情
(VI) 43400 5-allyl 1-benzyl 2-[[(2,2,2-trichloroethoxy)carbonyl]amino]pentanedioate C18H20Cl3NO6 详情 详情
(VII) 28271 decanoyl chloride 112-13-0 C10H19ClO 详情 详情
(VIII) 43401 5-allyl 1-benzyl 2-(decanoylamino)pentanedioate C25H37NO5 详情 详情
(IX) 43402 5-(benzyloxy)-4-(decanoylamino)-5-oxopentanoic acid C22H33NO5 详情 详情
(X) 43407 4-aminocyclohexylamine; 1,4-cyclohexanediamine 3114-70-3 C6H14N2 详情 详情
(XI) 43408 tert-butyl 4-aminocyclohexylcarbamate C11H22N2O2 详情 详情
(XII) 43409 benzyl 5-([4-[(tert-butoxycarbonyl)amino]cyclohexyl]amino)-2-(decanoylamino)-5-oxopentanoate C33H53N3O6 详情 详情
(XIII) 28277 2,5-diphenyl-1,3-oxazole-4-carboxylic acid C16H11NO3 详情 详情
(XIV) 43410 benzyl 2-(decanoylamino)-5-[(4-[[(2,5-diphenyl-1,3-oxazol-4-yl)carbonyl]amino]cyclohexyl)amino]-5-oxopentanoate C44H54N4O6 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

1,4-Diaminocyclohexane (I) is converted into the mono-carbamate (II) employing di-tert-butyl dicarbonate in cold THF. Subsequent reduction of carbamate (II) by means of LiAlH4 leads to the N-methyl amine (III). After blocking the primary amino group of (III) as the corresponding benzaldimine (IV), treatment with di-tert-butyl dicarbonate gives rise to the mono-protected diamine (V). (1,2)

1 Baxter, A.D.; Boyd, E.A.; Price, S.; Guicherit, O.M.; Porter, J.; Rubin, L.E. (Curis, Inc.); Small organic molecule regulators of cell proliferation. US 6613798; US 6683108; WO 0174344 .
2 Baxter, A.D.; Boyd, E.A.; Price, S.; Guicherit, O.M.; Porter, J.; Rubin, L.; Stibbard, J.H.A. (Curis, Inc.); Small organic molecule regulators of cell proliferation. US 2002198236; WO 0327234 .
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) 43407 4-aminocyclohexylamine; 1,4-cyclohexanediamine 3114-70-3 C6H14N2 详情 详情
(II) 43408 tert-butyl 4-aminocyclohexylcarbamate C11H22N2O2 详情 详情
(III) 63695 N~1~-methyl-1,4-cyclohexanediamine C7H16N2 详情 详情
(IV) 63696 N~1~-methyl-N~4~-(phenylmethylidene)-1,4-cyclohexanediamine C14H20N2 详情 详情
(V) 63697 1,1-dimethylethyl 4-aminocyclohexyl(methyl)carbamate C12H24N2O2 详情 详情
Extended Information