Chlorosuccinimide → HCID 178432846, compound

HRID 562002Notes

Reaction equation

HRID 562002 reaction equation
IC1C=CC([C:8]2[NH:12][C:11]([C@@H:13]([N:17]3[C:21](=[O:22])[C@@H:20]([CH2:23]CC(O)=O)[NH:19][C:18]3=[O:28])[CH:14]([CH3:16])[CH3:15])=[N:10][CH:9]=2)=CC=1.[Cl:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1I.[CH:38]1([CH2:41][C@H:42]2NC(=O)N([C@H](C3NC(C4C=CC(I)=CC=4F)=C(C)N=3)[C@H](C3C=CC=CC=3)C)C2=O)[CH2:40][CH2:39]1.[CH2:72]([Mg]Br)C.C(OC(N[C@H](C1C=CC(OCC(=O)N(C)C)=CC=1)C(O)=O)=O)(C)(C)C.ClN1C(=O)CCC1=O.C(OC(N[C@H](C1[CH:126]=[CH:125][C:124]([O:127][CH2:128][C@H:129]2[CH2:133][O:132]C(C)(C)[O:130]2)=[CH:123][CH:122]=1)C(O)=O)=O)(C)(C)C>>[Cl:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1[C:9]1[NH:10][C:11]([C@@H:13]([N:17]2[C:21](=[O:22])[C@@H:20]([C:23]3[CH:122]=[CH:123][C:124]([O:127][CH2:128][C@H:129]([OH:130])[CH2:133][OH:132])=[CH:125][CH:126]=3)[NH:19][C:18]2=[O:28])[C@H:14]([C:15]2[CH:42]=[CH:41][CH:38]=[CH:39][CH:40]=2)[CH3:16])=[N:12][C:8]=1[CH3:72]

Participants

8

Reactant 7

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 67001404(R)-tert-Butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acidHCID 178418443HCID 178418443, compoundHCID 178432851HCID 178432851, compound

Product 1

HCID 178432846HCID 178432846, compound

Procedure

Prepared by the same method as described in example 1 except that (i) in step 95-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 95-B ethylmagnesium bromide was used in place of methylmagnesium chloride; (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 95-F was omitted, and (iv) (R)-tert-butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid (prepared as described in steps 33-T and 33-U) was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 95-G. HR-MS: calcd for C31H30ClIN4O5 [M+H+] 701.1022. Found 701.1017.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-ed54bd9695704eab924b1d672593ca1d
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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