Ammonium Chloride → tert-butyl (5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oate

関与物質

役割	名称	HCID	仕込み量
反応物	Ammonium Chloride	HCID 25517	—
反応物	(2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-methylbutanoic acid	HCID 978328	—
反応物	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
反応物	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
反応物	(3R,4S,5S)-tert-butyl 4-((S)-2-amino-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate	HCID 10546343	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Ethyl Acetate	HCID 8857	—
生成物	tert-butyl (5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oate	HCID 71294595	—

反応手順

396 mg (1.1 mmol) N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valine was dissolved in DMF and then mixed in succession with 365 mg (1 mmol) tert-butyl-(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoate (intermediate 2), 234 mg (1.2 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 187 mg (1.2 mmol) 1-hydroxy-1H-benzotriazole hydrate. The mixture was stirred over night at RT. The batch was then poured into a mixture of 50% saturated aqueous ammonium chloride solution and ethyl acetate. The organic phase was separated, washed in succession with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was used directly in the next step without further purification.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09029406B2
出典データセット	uspto-grants-2015_05
ORD ID	ord-e3712feaf9394067bcf214276a8e8206
出典メモ	uspto-grants-2015_05