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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 561999Generated: October 31, 2026

Chlorosuccinimide → (R)-3-{(S)-1-[5-(2-Chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-butyl}-5-[4-(2-hydroxy-ethoxy)-phenyl]-imidazolidine-2,4-dione

https://huagongshe.com/reaction/561999

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChlorosuccinimideHCID 31398—
Reactant3-((R)-1-{(S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-methyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-propionic acidHCID 57771978—
Reactant(R)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acidHCID 66815126—
ReactantHCID 178432851HCID 178432851—
Product(R)-3-{(S)-1-[5-(2-Chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-butyl}-5-[4-(2-hydroxy-ethoxy)-phenyl]-imidazolidine-2,4-dioneHCID 57771946—

Reaction Steps

Prepared by the same method as described in example 1 except that (i) 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene in step 80-A; (ii) (S)-2-tert-butoxycarbonylamino-pentanoic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid in step 80-E; (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 80-F was omitted and (iv) removal of protecting groups and cyclization to form the hydantoin in step 80-H was performed as described in step 34-H. HR-MS: calcd for C24H24ClIN4O4 [M+H+] 595.0604. Found 595.0603.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08063085B2
Source datasetuspto-grants-2011_11
ORD IDord-4024b1645c4c479cb783c59135ab6e11
Source noteuspto-grants-2011_11