Hydrochloric Acid → HCID 178453516, compound

HRID 1404407Notes

Reaction equation

HRID 1404407 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([CH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][OH:23])[CH2:17][CH2:16]1)[CH2:9][CH2:10][NH:11][C:12](=[O:14])[O-:13])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+].Cl.[OH2:32]>C(Cl)(Cl)(Cl)Cl.C(#N)C.O.[Ru](Cl)(Cl)Cl>[CH3:4][C:1]([CH3:3])([O:5][C:6](=[O:24])[NH:7][CH:8]([C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][C:22]([OH:32])=[O:23])[CH2:17][CH2:16]1)[CH2:9][CH2:10][NH:11][C:12](=[O:13])[O:14][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23667635Sodium periodateHCID 131732179HCID 131732179, compound

Product 1

HCID 178453516HCID 178453516, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of the tert-butyl-1-(4-(2-hydroxyethyl)cyclohexyl)propane-1,3-diyldicarbamate (1.95 mmol), ruthenium (III) chloride hydrate (0.008 g, 0.039 mmol), sodium periodate (1.67 g, 2.8 mmol) in carbon tetrachloride (10 mL), acetonitrile (10 ml) and water (10 mL) was stirred at rt for 2 h. The reaction mixture was cooled to 0° C. and added 0.5N HCl (10 mL), extracted with DCM, dried over Na2SO4. Purification by flash column chromatography (eluent: 40% EtOAc in hexanes) gave the titled acid as white foam (0.67 g, 83%). LC/MC: 437.1 (MNa)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. customPurification by flash column chromatography (eluent: 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a562bac0215e4e26bd78b439afeeefdc
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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