【结 构 式】 |
【分子编号】25300 【品名】tert-butyl (1R)-1-benzyl-2-hydroxyethyl(methyl)carbamate 【CA登记号】 |
【 分 子 式 】C15H23NO3 【 分 子 量 】265.35256 【元素组成】C 67.9% H 8.74% N 5.28% O 18.09% |
合成路线1
该中间体在本合成路线中的序号:(I)N-Boc-N-Methyl-D-phenylalaninol (I) was oxidized to aldehyde (II) using SO3-pyridine complex. Reductive amination of (II) with benzylamine to yield (III), followed by hydrogenolytic debenzylation then furnished the monoprotected diamine (IV). This was condensed with methanesulfonyl chloride to yield sulfonamide (V). After deprotection of the Boc group of (V) with trifluoroacetic acid, amine (VI) was coupled with N-Boc-N-methyl-D-naphthylalanine (VII) using EDC and HOAt. The resulting amide (VIII) was further deprotected with trifluoroacetic acid, and then coupled with 5-(tert-butoxycarbonyl)amino-5-methyl-2-hexenoic acid (IX) to yield (X). Finally, acid deprotection of the Boc group of (X) furnished the target compound.
【1】 Hansen, B.S.; Peschke, B.; New growth hormone secretagogues: C-terminal modified sulfonamide-analogues of NN703. Bioorg Med Chem Lett 1999, 9, 9, 1295. |
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) | 25300 | tert-butyl (1R)-1-benzyl-2-hydroxyethyl(methyl)carbamate | C15H23NO3 | 详情 | 详情 | |
(II) | 25301 | tert-butyl (1R)-1-benzyl-2-oxoethyl(methyl)carbamate | C15H21NO3 | 详情 | 详情 | |
(III) | 25302 | tert-butyl (1R)-1-benzyl-2-(benzylamino)ethyl(methyl)carbamate | C22H30N2O2 | 详情 | 详情 | |
(IV) | 25303 | tert-butyl (1R)-2-amino-1-benzylethyl(methyl)carbamate | C15H24N2O2 | 详情 | 详情 | |
(V) | 25304 | tert-butyl (1R)-1-benzyl-2-[(methylsulfonyl)amino]ethyl(methyl)carbamate | C16H26N2O4S | 详情 | 详情 | |
(VI) | 25305 | N-[(2R)-2-(methylamino)-3-phenylpropyl]methanesulfonamide | C11H18N2O2S | 详情 | 详情 | |
(VII) | 22189 | (2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-(2-naphthyl)propionic acid | 147577-61-5 | C19H23NO4 | 详情 | 详情 |
(VIII) | 25306 | tert-butyl (1R)-2-[[(1R)-1-benzyl-2-[(methylsulfonyl)amino]ethyl](methyl)amino]-1-(2-naphthylmethyl)-2-oxoethyl(methyl)carbamate | C30H39N3O5S | 详情 | 详情 | |
(IX) | 22191 | (E)-5-[(tert-butoxycarbonyl)amino]-5-methyl-2-hexenoic acid | C12H21NO4 | 详情 | 详情 | |
(X) | 25307 | tert-butyl (E,7R,10R)-10-benzyl-1,1,6,9-tetramethyl-7-(2-naphthylmethyl)-5,8,13,13-tetraoxo-13lambda(6)-thia-6,9,12-triaza-3-tetradecen-1-ylcarbamate | C37H50N4O6S | 详情 | 详情 |