Hydrochloric Acid → HCID 46185756, compound

HRID 561975Notes

Reaction equation

HRID 561975 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]([N:22]3[C:26](=[O:27])[C@@H:25]([CH2:28][C:29]([NH:31][O:32][CH2:33][CH2:34][O:35]C=C)=[O:30])[NH:24][C:23]3=[O:38])[C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:35][CH2:34][CH2:33][O:32][NH:31][C:29](=[O:30])[CH2:28][C@@H:25]1[C:26](=[O:27])[N:22]([C@H:13]([C:11]2[NH:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=3)=[CH:9][N:10]=2)[C@H:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15])[C:23](=[O:38])[NH:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 46185509HCID 46185509, compound

Product 1

HCID 46185756HCID 46185756, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-((R)-1-{(1S,2S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-N-(2-vinyloxy-ethoxy)-acetamide (64 mg, 0.1 mmol) in methanol (3 mL) was added aqueous 1 N hydrochloric acid (3 mL). The mixture was stirred at room temperature for 3 hours. Saturated aqueous sodium carbonate solution (10 mL) was added and the reaction mixture was extracted with ethyl acetate (2×50 mL). The organic layers were successively washed with saturated aqueous sodium carbonate solution then brine, dried over sodium sulfate, filtered, concentrated and the residue purified by chromatography over silica gel gradient eluted from 100% methylene chloride up to 10% v/v methanol/methylene chloride during 30 minutes to give N-(2-hydroxy-ethoxy)-2-((R)-1-{(1S,2S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-acetamide as a white solid (42 mg, 61%). LC-MS: calcd for C25H26IN5O5 [M+H+] 604. Found 604.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (2×50 mL)
  2. washThe organic layers were successively washed with saturated aqueous sodium carbonate solution
  3. dry with materialbrine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue purified by chromatography over silica gel gradient
  7. washeluted from 100% methylene chloride up to 10% v/v methanol/methylene chloride during 30 minutes

Sources & evidence

ORD record
ord-2a05634b16194608b7e5fee973f8fe50
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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