Aspirin → HCID 66965415, compound

HRID 1359979Notes

Reaction equation

HRID 1359979 reaction equation
[C:1]([O:5][C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:13]([O:16][C:17]1[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:19]([OH:21])=[O:20])(=[O:15])[CH3:14].CCN=C=NCCCN(C)C.Cl.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.ClCCl.O1CCOCC1>[C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7].[C:13]([O:16][C:17]1[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:19]([OH:21])=[O:20])(=[O:15])[CH3:14]

Participants

7

Reactant 4

HCID 2244AspirinHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 66965415HCID 66965415, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 18626912Dioxane methylene chlorideSolvent

Procedure

Boc-aminopropanol (2.11 mmol), acetylsalicylic acid (2.11 mmol) (manufactured by Wako Pure Chemical Industries) and DMAP (0.42 mmol) were dissolved in dichloromethane-dioxane (2:1, 6 ml), and WSCI.HCl (2.35 mmol) was added thereto under ice-cooling. After returning to room temperature and stirring overnight, ethyl acetate was added thereto, followed by separation by washing with 5% citric acid, 5% sodium hydrogen carbonate and saturated brine consecutively. After dehydration drying with sodium sulfate, ethyl acetate was evaporated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, 0.5% triethylamine) to give the titled compound (298.0 mg, yield 48%). The structure was identified by 1H-NMR (CDCl3).

Workup

  1. temperatureunder ice-cooling
  2. customAfter returning to room temperature
  3. customfollowed by separation
  4. washby washing with 5% citric acid, 5% sodium hydrogen carbonate and saturated brine consecutively
  5. dry with materialAfter dehydration drying with sodium sulfate, ethyl acetate
  6. customwas evaporated under reduced pressure
  7. customThe thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, 0.5% triethylamine)

Sources & evidence

ORD record
ord-7ab2b43346be4b2d8a617122f1c0adc6
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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