Hydrochloric Acid → HCID 178502337, compound

HRID 1625504Notes

Reaction equation

HRID 1625504 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:46]([CH3:48])[CH3:47])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:18][C:17]2[CH:19]=[CH:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[N:30]=[C:31]([C@@H:34]5[CH2:38][CH2:37][CH2:36][N:35]5C(OC(C)(C)C)=O)[NH:32][CH:33]=4)=[CH:25][CH:24]=3)=[CH:22][C:16]=2[N:15]=1)=[O:8])=[O:4].[ClH:49].O1CCOCC1>CO>[Cl-:49].[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:46]([CH3:48])[CH3:47])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:18][C:17]2[CH:19]=[CH:20][C:21]([C:23]3[CH:24]=[CH:25][C:26]([C:29]4[NH+:30]=[C:31]([C@@H:34]5[CH2:38][CH2:37][CH2:36][NH2+:35]5)[NH:32][CH:33]=4)=[CH:27][CH:28]=3)=[CH:22][C:16]=2[N:15]=1)=[O:8])=[O:4].[Cl-:49]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178502336HCID 178502336, compound

Product 1

HCID 178502337HCID 178502337, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (2S)-2-[4-[4-[2-[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]pyrrolidin-2-yl]-1H-benzimidazol-5-yl]phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylate (100 mg, 0.1525 mmol) in MeOH (0.15 mL) is added HCl in dioxane (381.2 μL of 4 M, 1.525 mmol), stirred at rt overnight, then concentrated to afford 4-(4-(2-((S)-1-((S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-benzo[d]imidazol-5-yl)phenyl)-2-((S)-pyrrolidin-1-ium-2-yl)-1H-imidazol-3-ium chloride (100 mg, 0.1529 mmol, 100.3%) as a light brown solid. LC-MS shows presence of desired compound which is used as such in the next step without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-61c4a9ba9c74497fb460e04f05076feb
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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