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【结 构 式】

【分子编号】36985

【品名】tert-butyl 2-(6-[[(benzyloxy)carbonyl]amino]-1,2,3,4-tetrahydro-2-naphthalenyl)acetate

【CA登记号】

【 分 子 式 】C24H29NO4

【 分 子 量 】395.4986

【元素组成】C 72.89% H 7.39% N 3.54% O 16.18%

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:(VIIa)

Tetralone (I) was reduced with NaBH4 and the resulting alcohol (II) was dehydrated with p-TsOH in refluxing toluene to yield the dihydronaphthalene (III). Oxidation of (III) with N-methylmorpholine N-oxide and OsO4 produced diol (IV), which was converted to the 2-tetralone (V) by acid-catalyzed rearrangement. The unstable tetralone (V) was condensed with the sodium salt of tert-butyl diethyl phosphonoacetate (VI) providing a mixture of olefin isomers (VII). Catalytic hydrogenation of the olefin (VIIa-c) with simultaneous removal of the carbobenzoxy group furnished the aminotetralin (VIII). This was coupled with 4-cyanobenzoic acid (IX) using EDC to give amide (X). Addition of H2S to the nitrile group of (X), followed by S-methylation provided (XI). Then, displacement of the methylthio group of (XI) by ammonium acetate and further treatment with di-tert-butyl dicarbonate yielded the Boc-protected benzamidine (XII). Deprotection with trifluoroacetic acid produced the amidino acid (XIII), which was finally esterified with EtOH and HCl.

1 Fisher, M.J.; Arfstan, A.E.; Giese, U.; et al.; Fused bicyclic Gly-Asp beta-turn mimics with specific affinity for GPIIb-IIIa. J Med Chem 1999, 42, 23, 4875.
2 Fisher, M.J.; Happ, A.M.; Jakubowski, J.A.; Kinnick, M.D.; Kline, A.D.; Morin, J.M. Jr.; Sall, D.J.; Skelton, M.A.; Vasileff, R.T. (Eli Lilly and Company); Glycoprotein IIb/IIIa antagonists. CA 2128348; EP 0635492; JP 1996188564; US 5618843 .
3 Fisher, M.J.; Jakubowski, J.A.; Martinelli, M.J.; Morin, J.M. Jr.; Paal, M.; Ruhter, G.; Ruterbories, K.J.; Schotten, T.; Stenzel, W.; Vasileff, R.T. (Eli Lilly and Company); Glycoprotein IIb/IIIa antagonists. EP 0804431; JP 1999502194; WO 9622288 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIIa) 36985 tert-butyl 2-(6-[[(benzyloxy)carbonyl]amino]-1,2,3,4-tetrahydro-2-naphthalenyl)acetate C24H29NO4 详情 详情
(VIIb) 36986 (E)-tert-butyl 2-[6-[[(benzyloxy)carbonyl]amino]-3,4-dihydro-2(1H)-naphthalenylidene]acetate C24H27NO4 详情 详情
(VIIc) 36987 (Z)-tert-butyl 2-[6-[[(benzyloxy)carbonyl]amino]-3,4-dihydro-2(1H)-naphthalenylidene]acetate C24H27NO4 详情 详情
(I) 36980 benzyl 5-oxo-5,6,7,8-tetrahydro-2-naphthalenylcarbamate C18H17NO3 详情 详情
(II) 36981 benzyl 5-hydroxy-5,6,7,8-tetrahydro-2-naphthalenylcarbamate C18H19NO3 详情 详情
(III) 36982 benzyl 7,8-dihydro-2-naphthalenylcarbamate C18H17NO2 详情 详情
(IV) 36983 benzyl 5,6-dihydroxy-5,6,7,8-tetrahydro-2-naphthalenylcarbamate C18H19NO4 详情 详情
(V) 36984 benzyl 6-oxo-5,6,7,8-tetrahydro-2-naphthalenylcarbamate C18H17NO3 详情 详情
(VI) 25637 tert-butyl 2-(diethoxyphosphoryl)acetate 6273-47-8 C10H21O5P 详情 详情
(VIII) 36988 tert-butyl 2-(6-amino-1,2,3,4-tetrahydro-2-naphthalenyl)acetate C16H23NO2 详情 详情
(IX) 36897 4-cyanobenzoic acid;4-Carboxybenzonitrile;p-Carboxybenzonitrile 619-65-8 C8H5NO2 详情 详情
(X) 36989 tert-butyl 2-[6-[(4-cyanobenzoyl)amino]-1,2,3,4-tetrahydro-2-naphthalenyl]acetate C24H26N2O3 详情 详情
(XI) 36990 tert-butyl 2-[6-([4-[imino(methylsulfanyl)methyl]benzoyl]amino)-1,2,3,4-tetrahydro-2-naphthalenyl]acetate C25H30N2O3S 详情 详情
(XII) 36991 tert-butyl 2-[6-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]benzoyl]amino)-1,2,3,4-tetrahydro-2-naphthalenyl]acetate C29H37N3O5 详情 详情
(XIII) 36992 2-[6-([4-[amino(imino)methyl]benzoyl]amino)-1,2,3,4-tetrahydro-2-naphthalenyl]acetic acid C20H21N3O3 详情 详情
Extended Information