Chlorosuccinimide → HCID 178432851, compound

HRID 561976Notes

Reaction equation

HRID 561976 reaction equation
IC1C=CC(C2[NH:12][C:11]([C@@H:13]([N:17]3[C:21](=[O:22])[C@@H:20]([CH2:23][CH2:24][C:25](O)=O)[NH:19][C:18]3=[O:28])[CH:14]([CH3:16])[CH3:15])=[N:10]C=2)=CC=1.[F:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1[C:37](=O)[CH2:38][CH3:39].C(OC(N[C@H:49]([C:53]1C=CC(OCC(=O)N(C)C)=[CH:55][CH:54]=1)[C:50](O)=O)=O)(C)(C)C.ClN1C(=O)CC[C:68]1=O.C(OC(N[C@H](CC1CC1)C(O)=O)=O)(C)(C)C>>[CH:24]1([CH2:23][C@H:20]2[NH:19][C:18](=[O:28])[N:17]([C@H:13]([C:11]3[NH:10][C:37]([C:31]4[CH:32]=[CH:33][C:34]([I:36])=[CH:35][C:30]=4[F:29])=[C:38]([CH3:39])[N:12]=3)[C@H:14]([C:15]3[CH:55]=[CH:54][CH:53]=[CH:49][CH:50]=3)[CH3:16])[C:21]2=[O:22])[CH2:25][CH2:68]1

Participants

6

Reactant 5

HCID 31398ChlorosuccinimideHCID 2756015(R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acidHCID 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 670015461-(2-Fluoro-4-iodophenyl)propan-1-one

Product 1

HCID 178432851HCID 178432851, 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 below) was used in place of 1-(2-fluoro-4-iodo-phenyl)-ethanone in step 13-D; (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 13-F was omitted, and (iv) in step 13-G commercially available (R)-2-tert-butoxycarbonylamino-3-cyclopropyl-propionic acid was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-14db1c2a025a452dbe2b3c431ff02f52
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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