9H-fluoren-9-ylmethyl methyl[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]carbamate -Drug Synthesis Database

【结构式】

【分子编号】42291

【品名】9H-fluoren-9-ylmethyl methyl[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]carbamate

【CA登记号】

【分子式】C₂₆H₂₉N₃O₃S

【分子量】463.60068

【元素组成】C 67.36% H 6.31% N 9.06% O 10.35% S 6.92%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

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.

参考文献中间体

合成目标

【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	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

Extended Information