Chlorosuccinimide → HCID 178432848, compound

HRID 562001Notes

Reaction equation

HRID 562001 reaction equation
IC1C=CC(C2NC([C@@H](N3C(=O)[C@@H](CCC(O)=O)NC3=O)C(C)C)=NC=2)=CC=1.[Cl:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1I.C1(C[C@H]2NC(=O)[N:44]([C@H:48]([C:57]3[NH:58][C:59]([C:63]4C=CC(I)=CC=4F)=[C:60](C)[N:61]=3)[C@H:49]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH3:50])C2=O)CC1.C([Mg]Br)C.C(O[C:81]([NH:83][C@H:84]([C:88]1[CH:93]=[CH:92][C:91]([O:94][CH2:95][C:96](=[O:100])N(C)C)=[CH:90][CH:89]=1)[C:85]([OH:87])=O)=[O:82])(C)(C)C.ClN1C(=O)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:85](=[O:87])[C@@H:84]([C:88]3[CH:89]=[CH:90][C:91]([O:94][CH2:95][CH2:96][OH:100])=[CH:92][CH:93]=3)[NH:83][C:81]2=[O:82])[C@H:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH3:50])=[N:58][C:59]=1[CH3:63]

Participants

7

Reactant 6

HCID 31398ChlorosuccinimideHCID 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 66815126(R)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acidHCID 178418443HCID 178418443, compoundHCID 178432851HCID 178432851, compound

Product 1

HCID 178432848HCID 178432848, compound

Procedure

Prepared by the same method as described in example 1 except that (i) in step 94-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 93-B ethylmagnesium bromide was used in place of methylmagnesium chloride and (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 94-F was omitted. HR-MS: calcd for C30H28ClIN4O4 [M+H+] 671.0917. Found 671.0917.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-a71b623560fb42379109dd1f64bf080c
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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