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【结 构 式】 
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【分子编号】30316 【品名】(2R)-2-amino-3-[(2-aminoethyl)amino]-1-propanol 【CA登记号】 |
【 分 子 式 】C5H15N3O 【 分 子 量 】133.19372 【元素组成】C 45.09% H 11.35% N 31.55% O 12.01% |
合成路线1
该中间体在本合成路线中的序号：(IV)The amidation of L-serine methyl ester (I) with ethylenediamine (II) gives the amide (III), which is reduced with borane/THF to 2(R)-(hydroxymethyl)diethylenetriamine (IV). The reaction of (IV) with bromoacetic acid tert-butyl ester (V) by means of DIEA in DMF affords the penta tert-butyl acetate (VI), which is condensed with the chlorophosphoramidite (VII) by means of DIEA in dichloromethane giving the phosphoramidite intermediate (VIII). The condensation of (VIII) with 4,4-diphenylcyclohexanol (IX) (see scheme 23537901b) by means of tetrazole in acetonitile, with simultaneous oxidation with tert-butyl hydroperoxide yields the phosphate (X), which is selectively hydrolyzed at the 2-cyanoethyl ester group with ammonia in methanol affording the ammonium phosphate (XI). Finally, the hydrolysis of (XI) with HCl in ether/water eliminates the tert-butyl groups affording the desired chelating ligand (XII)
| 【1】 Scott, D.M.; Sajiki, H.; McMurray, T.J.; Lauffer, R.B. (Epix Medical, Inc.); Diagnostic imaging contrast agents with extended blood retention. WO 9623526 . |
| 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) | 20915 | methyl (2S)-2-amino-3-hydroxypropanoate | 5680-80-8 | C4H9NO3 | 详情 | 详情 |
| (II) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |
| (III) | 30315 | (2S)-2-amino-N-(2-aminoethyl)-3-hydroxypropanamide | C5H13N3O2 | 详情 | 详情 | |
| (IV) | 30316 | (2R)-2-amino-3-[(2-aminoethyl)amino]-1-propanol | C5H15N3O | 详情 | 详情 | |
| (V) | 17430 | 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate | 5292-43-3 | C6H11BrO2 | 详情 | 详情 |
| (VI) | 30317 | 3,6,9-Tris(tert-butoxycarbonylmethyl)-4(R)-(hydroxymethyl)-3,6,9-triazaundecanedioic acid di-tert-butyl ester | C35H65N3O11 | 详情 | 详情 | |
| (VII) | 22791 | 2-Cyanoethyl N,N-diisopropylphosphoramidochloridite | 89992-70-1 | C9H18ClN2OP | 详情 | 详情 |
| (VIII) | 30318 | 3,6,9-Tris(tert-butoxycarbonylmethyl)-4(R)-[2-cyanoethoxy(diisopropylamino)phosphinyloxymethyl]-3,6,9-triazaundecanedioic acid di-tert-butyl ester | C44H82N5O12P | 详情 | 详情 | |
| (IX) | 30319 | 4,4-diphenylcyclohexanol | C18H20O | 详情 | 详情 | |
| (X) | 30320 | 3,6,9-Tris(tert-butoxycarbonylmethyl)-4(R)-[2-cyanoethoxy(4,4-diphenylcyclohexyloxy)phosphoryloxymethyl]-3,6,9-triazaundecanedioic acid di-tert-butyl ester | C56H87N4O14P | 详情 | 详情 | |
| (XI) | 30321 | 3,6,9-Tris(tert-butoxycarbonylmethyl)-4(R)-[4,4-diphenylcyclohexyloxy(hydroxy)phosphoryloxymethyl]-3,6,9-triazaundecanedioic acid di-tert-butyl ester ammonium salt | C53H87N4O14P | 详情 | 详情 | |
| (XII) | 30322 | 3,6,9-Tris(carboxymethyl)-4(R)-[4,4-diphenylcyclohexyloxy(hydroxy)phosphoryloxymethyl]-3,6,9-triazaundecanedioic acid | C33H44N3O14P | 详情 | 详情 |