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

HRID 562000Notes

Reaction equation

HRID 562000 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5](C2NC([C@@H](N3C(=O)[C@@H](CCC(O)=O)NC3=O)C(C)C)=NC=2)=[CH:4][CH:3]=1.[Cl:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1I.C1(C[C@H:42]2[NH:46][C:45](=[O:47])[N:44]([C@H:48]([C:57]3[NH:58][C:59](C4C=CC(I)=CC=4F)=[C:60](C)[N:61]=3)[C@H:49]([C:51]3[CH:56]=CC=C[CH:52]=3)C)[C:43]2=[O:71])CC1.C(OC(N[C@@H:80](CC(C)C)[C:81]([OH:83])=O)=O)(C)(C)C.ClN1C(=[O:94])CCC1=O>>[Cl:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1[C:60]1[NH:61][C:57]([C@@H:48]([N:44]2[C:43](=[O:71])[C@@H:42]([C:2]3[CH:3]=[CH:4][C:5]([O:94][CH2:80][CH2:81][OH:83])=[CH:6][CH:7]=3)[NH:46][C:45]2=[O:47])[CH2:49][CH:51]([CH3:56])[CH3:52])=[N:58][CH:59]=1

Participants

6

Reactant 5

HCID 31398ChlorosuccinimideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 534065552-Chloro-1,4-diiodobenzeneHCID 577719783-((R)-1-{(S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-methyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-propionic acidHCID 178432851HCID 178432851, compound2×

Product 1

HCID 57771887(R)-3-{(S)-1-[5-(2-Chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-3-methyl-butyl}-5-[4-(2-hydroxy-ethoxy)-phenyl]-imidazolidine-2,4-dione

Procedure

Prepared by the same method as described in example 1 except that (i) in step 82-A step 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 82-E (S)-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid, and (ii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 82-F was omitted. HR-MS: calcd for C25H26ClIN4O4 [M+H+] 609.0760. Found 609.0757.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-318321fac2044e15add962df60581aec
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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