Trifluoroacetic acid → (S)-N-(4-Iodo-phenyl)-2-[(R)-4-(4-methoxy-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-phenyl-propionamide

HRID 1433750Notes

Reaction equation

HRID 1433750 reaction equation
C(OC(N[C@@H](CC1C=CC=CC=1)C(O)=O)=O)(C)(C)C.C(O[C:25]([NH:27][C@H:28]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C@H]2COC(C)(C)O2)=[CH:34][CH:33]=1)[C:29]([OH:31])=O)=[O:26])(C)(C)C.FC(F)(F)C(O)=O.[NH2:54][C@@H:55]([CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[C:56]([NH:58][C:59]1[CH:64]=[CH:63][C:62]([I:65])=[CH:61][CH:60]=1)=[O:57].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>>[I:65][C:62]1[CH:63]=[CH:64][C:59]([NH:58][C:56](=[O:57])[C@@H:55]([N:54]2[C:29](=[O:31])[C@@H:28]([C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)[NH:27][C:25]2=[O:26])[CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)=[CH:60][CH:61]=1

Participants

8

Reactant 7

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28976652HCID 28976652, compoundHCID 67001404(R)-tert-Butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid

Product 1

HCID 57935156(S)-N-(4-Iodo-phenyl)-2-[(R)-4-(4-methoxy-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-phenyl-propionamide

Procedure

Prepared by the same method as described in example 1 except that (i) (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid in step 1, (ii) 4-iodoaniline was used in place of 4-bromoaniline in step 2, and (iii) the trifluoroacetic acid salt of (S)-2-amino-N-(4-iodo-phenyl)-3-phenyl-propionamide was isolated in step 3 and used directly in step 4 with 1.0 equivalent of triethylamine and (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride as the coupling reagent in place of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexaflurorophosphate.

Workup

  1. customPrepared by the same method
  2. customwas isolated in step 3

Sources & evidence

ORD record
ord-651c6c2b9fe645caac3a281726f7d2f4
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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