Chlorosuccinimide → (r)-3-{(s)-1-[5-(4-Bromo-phenyl)-4-methyl-1h-imidazol-2-yl]-2-phenyl-ethyl}-5-[4-(2-hydroxy-ethoxy)-phenyl]-imidazolidine-2,4-dione

HRID 562003Notes

Reaction equation

HRID 562003 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:33]2[NH:37][C:36](=[O:38])[N:35]([C@H:39]([C:48]3[NH:49]C(C4C=CC(I)=CC=4F)=C(C)[N:52]=3)[C@H:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)C)[C:34]2=[O:62])CC1.[Br:63][C:64]1[CH:69]=[CH:68][C:67]([C:70](=O)[CH2:71][CH3:72])=[CH:66][CH:65]=1.C(OC(N[C@H]([C:86]1[CH:91]=[CH:90][C:89]([O:92][CH2:93][C:94](=[O:98])N(C)C)=[CH:88][CH:87]=1)C(O)=O)=O)(C)(C)C.ClN1C(=O)CCC1=O>>[Br:63][C:64]1[CH:69]=[CH:68][C:67]([C:70]2[NH:52][C:48]([C@@H:39]([N:35]3[C:34](=[O:62])[C@@H:33]([C:86]4[CH:91]=[CH:90][C:89]([O:92][CH2:93][CH2:94][OH:98])=[CH:88][CH:87]=4)[NH:37][C:36]3=[O:38])[CH2:40][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[N:49][C:71]=2[CH3:72])=[CH:66][CH:65]=1

Participants

6

Reactant 5

HCID 31398ChlorosuccinimideHCID 66312p-BromopropiophenoneHCID 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 178432844(r)-3-{(s)-1-[5-(4-Bromo-phenyl)-4-methyl-1h-imidazol-2-yl]-2-phenyl-ethyl}-5-[4-(2-hydroxy-ethoxy)-phenyl]-imidazolidine-2,4-dione

Procedure

Prepared by the same method as described in example 1 except that (i) steps A, B and C were omitted; (ii) commercially available 1-(4-bromo-phenyl)-propan-1-one was used in place of 1-(2-fluoro-4-iodo-phenyl)-ethanone in step 105-D; (iii) (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid in step 105-E and (iv) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 105-F was omitted. HR-MS: calcd for C29H27BrN4O4 [M+H+] 575.1289. Found 575.1286.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-2ec1eb78923b4879a51523e321442b6c
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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