Chlorotrimethylsilane → (R)-3-{(S)-1-[5-(4-Iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-5-prop-2-ynyl-imidazolidine-2,4-dione

https://huagongshe.com/reaction/561980

関与物質

役割	名称	HCID	仕込み量
反応物	Chlorotrimethylsilane	HCID 6397	—
反応物	Trifluoroacetic acid	HCID 6422	—
反応物	Chlorosuccinimide	HCID 31398	—
反応物	1-(4-Iodophenyl)ethan-1-one	HCID 72869	—
反応物	(2R)-2-(((tert-butoxy)carbonyl)amino)pent-4-ynoic acid	HCID 7009126	—
反応物	3-((R)-1-{(S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-methyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-propionic acid	HCID 57771978	—
反応物	(R)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acid	HCID 66815126	—
反応物	{(1S,2S)-1-[5-(2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-carbamic acid tert-butyl ester	HCID 67001749	—
溶媒	Formic Acid	HCID 284	—
溶媒	Triethylamine	HCID 8471	—
生成物	(R)-3-{(S)-1-[5-(4-Iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-5-prop-2-ynyl-imidazolidine-2,4-dione	HCID 57771957	—

反応手順

Prepared by the same method as described in example 1 except that (i) steps A, B, and C were omitted; (ii) commercially available 1-(4-iodo-phenyl)-ethanone was used in place of 1-(2-fluoro-4-iodo-phenyl)-ethanone in step 18-D; (iii) (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid in step 18-E; (iv) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 18-F was omitted; (v) (R)-2-tert-butoxycarbonylamino-pent-4-ynoic acid was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 18-G; and (vi) in step 18-H, formic acid (neat) heated to 30° C. was used in place of trifluoroacetic acid and silylation with chlorotrimethylsilane and triethylamine was omitted. HR-MS: calcd for C23H19IN4O2 [M+H+] 511.0626. Found 511.0623.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08063085B2
出典データセット	uspto-grants-2011_11
ORD ID	ord-2b33d7d6a5364198ae27a67094cfe5af
出典メモ	uspto-grants-2011_11