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【结 构 式】 
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【分子编号】34526 【品名】2-[(3-[[(10S)-10-(2-ethoxy-2-oxoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-3-yl]oxy]propyl)amino]-1-pyridiniumolate 【CA登记号】 |
【 分 子 式 】C27H30N2O4 【 分 子 量 】446.54628 【元素组成】C 72.62% H 6.77% N 6.27% O 14.33% |
合成路线1
该中间体在本合成路线中的序号：(XIV)Condensation of 2-chloropyridine-N-oxide hydrochloride (XI) with 3-amino-1-propanol (XII) in boiling tert-amyl alcohol provided the aminopyridine N-oxide (XIII). Subsequent Mitsunobu coupling of (XIII) with the chiral phenol (X) in the presence of diisopropyl azodicarboxylate and triphenyl phosphine produced ether (XIV). The N-oxide group of (XIV) was then reduced by transfer hydrogenation using cyclohexene and Pd/C to yield pyridine (XV). Finally, saponification of the ethyl ester of (XV) furnished the title compound.
| 【1】 Drake, F.H. (SmithKline Beecham plc); Method for stimulating bone formation. EP 0946180; WO 9815278 . |
| 【2】 Miller, W.H.; Samanen, J.M.; Heerding, D.; Bondinell, W.E. (SmithKline Beecham Corp.); Vitronectin receptor antagonists. EP 1025090; WO 9915508 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 34523 | ethyl 2-[(10S)-3-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl]acetate | C19H20O3 | 详情 | 详情 | |
| (XI) | 34524 | 2-chloro-1-pyridiniumolate | 2402-95-1 | C5H4ClNO | 详情 | 详情 |
| (XII) | 18522 | 3-amino-1-propanol | 156-87-6 | C3H9NO | 详情 | 详情 |
| (XIII) | 34525 | 2-[(3-hydroxypropyl)amino]-1-pyridiniumolate | C8H12N2O2 | 详情 | 详情 | |
| (XIV) | 34526 | 2-[(3-[[(10S)-10-(2-ethoxy-2-oxoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-3-yl]oxy]propyl)amino]-1-pyridiniumolate | C27H30N2O4 | 详情 | 详情 | |
| (XV) | 34527 | ethyl 2-[(10S)-3-[3-(2-pyridinylamino)propoxy]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl]acetate | C27H30N2O3 | 详情 | 详情 |