Hydrochloric Acid → HCID 6476732, compound

HRID 1018287Notes

Reaction equation

HRID 1018287 reaction equation
I[NH:2][C@H](C(O)=O)CC1C=CC(O)=CC=1.[C:15]([O:19]C)(=[O:18])[CH:16]=[CH2:17].[C:21]([NH:28][C@H:29]([C:38]([OH:40])=O)[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)([O:23]C(C)(C)C)=O.Cl.[CH:42]1([N:48]2[C:52]3[CH:53]=[CH:54][C:55](C(O)=O)=[CH:56][C:51]=3[N:50]=[C:49]2[C:60]2[CH:64]=[CH:63][O:62][CH:61]=2)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>O1CCOCC1>[C:38]([C@@H:29]([NH:28][C:21]([C:55]1[CH:54]=[CH:53][C:52]2[N:48]([CH:42]3[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]3)[C:49]([C:60]3[CH:64]=[CH:63][O:62][CH:61]=3)=[N:50][C:51]=2[CH:56]=1)=[O:23])[CH2:30][C:31]1[CH:32]=[CH:33][C:34]([OH:37])=[C:35](/[CH:17]=[CH:16]/[C:15]([OH:19])=[O:18])[CH:36]=1)(=[O:40])[NH2:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 303285729592-76-5

Product 1

HCID 6476732HCID 6476732, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The iodo tyrosine derivative prepared above was coupled to methyl acrylate according to the procedure of example 83: MS (ES+) m/z 307 (MH+-Boc). The N-Boc-tyrosine derivative prepared above was deprotected with 4 N HCl in dioxane and coupled with the acid of example 2 in the usual manner. Following saponification of the O-acetyl group the title compound of example 142 was obtained.

Sources & evidence

ORD record
ord-ffa47744cdfa4f0589f4b9ea34ae8bc4
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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