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【结 构 式】 
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【分子编号】24997 【品名】7-cyano-2-naphthyl trifluoromethanesulfonate 【CA登记号】 |
【 分 子 式 】C12H6F3NO3S 【 分 子 量 】301.2457896 【元素组成】C 47.85% H 2.01% F 18.92% N 4.65% O 15.93% S 10.64% |
合成路线1
该中间体在本合成路线中的序号：(V)A new synthesis of 2-[4-[1-(tert-butoxycarbonyl)pyrrolidin-3(S)-yloxy)phenyl]-3-(7-cyano-2-naphthyl)-2-propenoic acid ethyl ester (VI), a key intermediate in the synthesis of DX-9065a has been described: The condensation of 3(R)-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (I) with 4-hydroxyphenylacetic acid ethyl ester (II) by means of triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF gives 4-[1-(tert-butoxycarbonyl)pyrrolidin-3(R)-yloxy]phenylacetic acid ethyl ester (III), which is treated with formaldehyde, K2CO3 and tetrabutylammonium iodide in hot toluene yielding 2-[4-[1-(tert-butoxycarbonyl)pyrrolidin-3(R)-yloxy]phenyl]-2-propenoic acid ethyl ester (IV). Finally, this compound is condensed with 7-(trifluoromethylsulfonyloxy)naphthalene-2-carbonitrile (V) by means a Pd catalyst in hot DMF to afford the target compound (VI).
| 【1】 Yokoyama, Y.; Synthesis of specific factor Xa inhibitor, DX-9065a. Symp Med Chem 1998, Abst L-15. |
| 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) | 16286 | tert-butyl (3S)-3-hydroxytetrahydro-1H-pyrrole-1-carboxylate | C9H17NO3 | 详情 | 详情 | |
| (II) | 24994 | Ethyl 2-(4-hydroxyphenyl)acetate | 17138-28-2 | C10H12O3 | 详情 | 详情 |
| (III) | 24989 | tert-butyl (3S)-3-[4-(2-ethoxy-2-oxoethyl)phenoxy]-1-pyrrolidinecarboxylate | C19H27NO5 | 详情 | 详情 | |
| (IV) | 24996 | tert-butyl (3S)-3-[4-[1-(ethoxycarbonyl)vinyl]phenoxy]-1-pyrrolidinecarboxylate | C20H27NO5 | 详情 | 详情 | |
| (V) | 24997 | 7-cyano-2-naphthyl trifluoromethanesulfonate | C12H6F3NO3S | 详情 | 详情 | |
| (VI) | 16290 | tert-butyl (3S)-3-[4-[(Z)-2-(7-cyano-2-naphthyl)-1-(ethoxycarbonyl)ethenyl]phenoxy]-1-pyrrolidinecarboxylate | C31H32N2O5 | 详情 | 详情 | |
| (VII) | 24999 | 7-methoxy-3,4-dihydro-2(1H)-naphthalenone | 4133-34-0 | C11H12O2 | 详情 | 详情 |
| (VIII) | 25000 | 7-methoxy-3,4-dihydro-2-naphthalenecarbonitrile | C12H11NO | 详情 | 详情 | |
| (IX) | 25001 | 7-methoxy-2-naphthonitrile | C12H9NO | 详情 | 详情 | |
| (X) | 25002 | 7-hydroxy-2-naphthonitrile | C11H7NO | 详情 | 详情 | |
| (XI) | 25003 | 7-methoxy-2-naphthol | 5060-82-2 | C11H10O2 | 详情 | 详情 |
| (XII) | 25004 | 7-methoxy-2-naphthyl trifluoromethanesulfonate | C12H9F3O4S | 详情 | 详情 |