1,4-Dioxane hydrochloride → HCID 74983022, compound

HRID 332620Notes

Reaction equation

HRID 332620 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([O:10][C:11](=[O:42])[CH:12]([CH2:36][C:37]([O:39]CC)=[O:38])[S:13][C:14](=[O:35])[CH:15]([CH3:34])[CH2:16][C:17]1[O:18][C:19]([C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31](=[NH:33])[NH2:32])=[CH:27][CH:26]=2)=[O:23])=[CH:20][CH:21]=1)C.Cl.O1CCOCC1>O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:31]([C:28]1[CH:27]=[CH:26][C:25]([O:24][C:22]([C:19]2[O:18][C:17]([CH2:16][CH:15]([CH3:34])[C:14]([S:13][CH:12]([CH2:36][C:37]([OH:39])=[O:38])[C:11]([OH:42])=[O:10])=[O:35])=[CH:21][CH:20]=2)=[O:23])=[CH:30][CH:29]=1)(=[NH:32])[NH2:33]

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86673325HCID 86673325, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 74983022HCID 74983022, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To S-{3-[5-(4-amidinophenoxycarbonyl)furan-2-yl]-2-methylpropionyl}thiomalic acid diethyl ester trifluoroacetic acid salt (40 mg, 0.065 mmol) obtained in step 1 was added 4N hydrochloric acid/dioxane solution:water=3:1 (500 μL), and the mixture was stirred at 60° C. overnight. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by high performance liquid chromatography (acetonitrile-water, each containing 0.1% trifluoroacetic acid, 10-45%) to give the title compound (5.0 mg, 0.0089 mmol, 14%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by high performance liquid chromatography (acetonitrile-water

Sources & evidence

ORD record
ord-79f037bd1d1941f1921784743e361cbe
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

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