Chlorosuccinimide → HCID 178432850, compound

HRID 561994Notes

Reaction equation

HRID 561994 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]=4[F:61])=[C:51]([CH3:53])[N:52]=3)[C@H:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH3:41])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:84]([CH3:86])[CH3:85])=[CH:77][CH:76]=1)[C:72]([OH:74])=O)=[O:69])(C)(C)C.ClN1C(=O)CCC1=O>>[F:61][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][C:83]([N:84]([CH3:85])[CH3:86])=[O:87])=[CH:79][CH:80]=3)[NH:70][C:68]2=[O:69])[C@H:40]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH3:41])=[N:52][C:51]=1[CH3:53]

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 acid2×HCID 178432851HCID 178432851, compound

Product 1

HCID 178432850HCID 178432850, compound

Procedure

Prepared by the same method as described in example 1 except that (i) steps A, B and C were omitted; (ii) 1-(2-fluoro-4-iodo-phenyl)-propan-1-one (prepared as described in example 13) was used in place of 1-(2-fluoro-4-iodo-phenyl)-ethanone in step 72-D; (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 72-F was omitted and (iv) (R)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acid (prepared as described in example 6) was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 72-G. HR-MS: calcd for C32H31FlN5O4 [M+H+] 696.1478. Found 696.1475.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-87f188de6342464095deb3372e0bef4d
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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