【结 构 式】 |
【分子编号】42293 【品名】(2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(2-naphthyl)propionic acid 【CA登记号】 |
【 分 子 式 】C29H25NO4 【 分 子 量 】451.52184 【元素组成】C 77.14% H 5.58% N 3.1% O 14.17% |
合成路线1
该中间体在本合成路线中的序号:(V)The title compound was prepared by stepwise peptide synthesis starting from N-Fmoc-N-methyl-D-thienylalanine (I), which was condensed with trimethyl hydrazine (II) to give hydrazide (III). Removal of the Fmoc protecting group with piperidine in DMF provided amine (IV), which was subsequently coupled with N-methyl-D-naphthylalanine (V) in the presence of EDC and HOAt to furnish the dipeptide hydrazide (VI). After removal of the Fmoc group of (VI) with piperidine, the resulting amine (VII) was coupled with N-Boc-5-amino-5-methylhex-2-enoic acid (VIII), yielding amide (IX). Final deprotection of the Boc group of (IX) using trifluoroacetic acid afforded the title compound.
【1】 Hansen, B.S.; Ankersen, M.; Nielsen, K.K.; Hansen, T.K.; Raun, K.; Growth hormone secretagogues derived from NN703 with hydrazides as c-terminal. Eur J Med Chem 2000, 35, 5, 487. |
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) | 42289 | (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(2-thienyl)propionic acid | C23H21NO4S | 详情 | 详情 | |
(II) | 42290 | 1,1,2-trimethylhydrazine | C3H10N2 | 详情 | 详情 | |
(III) | 42291 | 9H-fluoren-9-ylmethyl methyl[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]carbamate | C26H29N3O3S | 详情 | 详情 | |
(IV) | 42292 | (2R)-N,N',N'-trimethyl-2-(methylamino)-3-(2-thienyl)propanohydrazide | C11H19N3OS | 详情 | 详情 | |
(V) | 42293 | (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(2-naphthyl)propionic acid | C29H25NO4 | 详情 | 详情 | |
(VI) | 42294 | 9H-fluoren-9-ylmethyl methyl[(1R)-2-[methyl[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]amino]-1-(2-naphthylmethyl)-2-oxoethyl]carbamate | C40H42N4O4S | 详情 | 详情 | |
(VII) | 42295 | (2R)-N-methyl-2-(methylamino)-3-(2-naphthyl)-N-[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]propanamide | C25H32N4O2S | 详情 | 详情 | |
(VIII) | 22191 | (E)-5-[(tert-butoxycarbonyl)amino]-5-methyl-2-hexenoic acid | C12H21NO4 | 详情 | 详情 | |
(IX) | 42296 | tert-butyl (E)-1,1-dimethyl-5-[methyl[(1R)-2-[methyl[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]amino]-1-(2-naphthylmethyl)-2-oxoethyl]amino]-5-oxo-3-pentenylcarbamate | C37H51N5O5S | 详情 | 详情 |