|
【结 构 式】 
|
【分子编号】41219 【品名】tert-butyl (1S)-1-benzyl-2-[[(3R)-1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]amino]-2-oxoethylcarbamate 【CA登记号】 |
【 分 子 式 】C34H44N4O5 【 分 子 量 】588.74732 【元素组成】C 69.36% H 7.53% N 9.52% O 13.59% |
合成路线1
该中间体在本合成路线中的序号：(IIIb)The condensation of 3-amino-1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (I) with N-(tert-butoxycarbonyl)-L-phenylalanine (II) by means of HOBT and WSCD in DMF gives the corresponding amide as a diastereomeric mixture (IIIa-b), which is deprotected at the Boc group by treatment with HCl in ethyl acetate yielding the diastereomeric mixture of L-phenylalanine amides (IVa-b). The HPLC chromatographic separation of both diastereomers affords pure (Va) and (Vb). The desired diastereomer (Va) is treated with phenyl isothiocyanate (VI) to provide the chiral amine (R)-(VII), which is finally condensed with 3-methylphenyl isocyanate (VIII) to furnish the target urea.
| 【1】 Toyoda, T.; Adachi, M.; Sugasawa, T.; et al.; Aminohaloborane in organic synthesis. I. Specific ortho substitution reaction of anilines. J Am Chem Soc 1978, 100, 4842. |
| 【2】 Satoh, Y.; Tabuchi, S.; Mitsui, H.; Design of dual CCK-A and CCK-B receptor antagonists. Drugs Fut 1997, 22, 10, 1117. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IIIa) | 41214 | tert-butyl (1S)-1-benzyl-2-[[(3S)-1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]amino]-2-oxoethylcarbamate | C34H44N4O5 | 详情 | 详情 | |
| (Va) | 41216 | (2S)-2-amino-N-[(3R)-1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]-3-phenylpropanamide | C29H36N4O3 | 详情 | 详情 | |
| (Vb) | 41217 | (2S)-2-amino-N-[(3S)-1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]-3-phenylpropanamide | C29H36N4O3 | 详情 | 详情 | |
| (IIIb) | 41219 | tert-butyl (1S)-1-benzyl-2-[[(3R)-1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]amino]-2-oxoethylcarbamate | C34H44N4O5 | 详情 | 详情 | |
| (I) | 41213 | 3-amino-1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one | C20H27N3O2 | 详情 | 详情 | |
| (II) | 12874 | (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine | 13734-34-4 | C14H19NO4 | 详情 | 详情 |
| (IV) | 41215 | (2S)-2-amino-N-[1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]-3-phenylpropanamide | C29H36N4O3 | 详情 | 详情 | |
| (VI) | 22146 | 1-isothiocyanatobenzene; phenyl isothiocyanate | 103-72-0 | C7H5NS | 详情 | 详情 |
| (VII) | 41218 | (3R)-3-amino-1-(2-cyclohexyl-2-oxoethyl)-5-ethyl-9-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one | C20H27N3O2 | 详情 | 详情 | |
| (VIII) | 18071 | m-Tolyl Isocyanate; 1-isocyanato-3-methylbenzene; 3-methylphenyl isocyanate | 621-29-4 | C8H7NO | 详情 | 详情 |