Chlorosuccinimide → HCID 57771946, compound

HRID 561999Notes

Reaction equation

HRID 561999 reaction equation
IC1C=CC(C2NC([C@@H](N3C(=O)[C@@H](CCC(O)=O)NC3=O)C(C)C)=NC=2)=CC=1.C1(C[C@H]2NC(=O)[N:35]([C@H:39]([C:48]3[NH:49][C:50]([C:54]4[CH:59]=[CH:58][C:57]([I:60])=[CH:56][C:55]=4F)=[C:51](C)[N:52]=3)[C@H:40]([C:42]3C=CC=C[CH:43]=3)C)C2=O)CC1.C(O[C:68]([NH:70][C@H:71]([C:75]1[CH:80]=[CH:79][C:78]([O:81][CH2:82][C:83](=[O:87])N(C)C)=[CH:77][CH:76]=1)[C:72]([OH:74])=O)=[O:69])(C)(C)C.[Cl:88]N1C(=O)CCC1=O>>[Cl:88][C:55]1[CH:56]=[C:57]([I:60])[CH:58]=[CH:59][C:54]=1[C:50]1[NH:49][C:48]([C@@H:39]([N:35]2[C:72](=[O:74])[C@@H:71]([C:75]3[CH:76]=[CH:77][C:78]([O:81][CH2:82][CH2:83][OH:87])=[CH:79][CH:80]=3)[NH:70][C:68]2=[O:69])[CH2:40][CH2:42][CH3:43])=[N:52][CH:51]=1

Participants

5

Reactant 4

HCID 31398ChlorosuccinimideHCID 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 178432851HCID 178432851, compound

Product 1

HCID 57771946HCID 57771946, compound

Procedure

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.

Workup

  1. customPrepared by the same method
  2. custom(iv) removal of protecting groups and cyclization

Sources & evidence

ORD record
ord-4024b1645c4c479cb783c59135ab6e11
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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