p-Toluenesulfonic acid → HCID 86619058, compound

HRID 1365551Notes

Reaction equation

HRID 1365551 reaction equation
C(=O)([O-])O.[Na+].Cl.[NH2:7][CH2:8][C:9](=[O:21])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:13].[C:22]1(C)[CH:27]=[CH:26][C:25]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1>O.ClCCl>[C:24]1([CH3:8])[C:25]([S:28]([OH:31])(=[O:29])=[O:30])=[CH:26][CH:27]=[CH:22][CH:23]=1.[NH2:7][CH2:8][C:9](=[O:21])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:13]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 6433082Hexaminolevulinate hydrochloride

Product 1

HCID 86619058HCID 86619058, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium hydrogen carbonate (0.42 g; 5.0 mmol) was added to a solution of hexyl 5-amino-4-oxopentanoate hydrochloride (0.5 g; 2.0 mmol) in water (10 ml) and dichloromethane (5 ml). The mixture was shaken thoroughly and allowed to separate. The organic layer was pipetted off and added to p-toluenesulfonic acid (0.38 g; 2.0 mmol). The aqueous portion was extracted with dichloromethane (1×1 ml). The combined organic solutions were evaporated, leaving a yellow oil that solidified on overnight storage in a freezer. The residue was purified by flash chromatography on a 170×25 mm silica gel 60 column eluted with acetonitrile (150 ml), 5% methanol in acetonitrile (500 ml), and 10% methanol in acetonitrile (250 ml), collecting 15×50 ml fractions. Fractions containing the product were evaporated, leaving 0.31 g (40%) residue.

Workup

  1. customto separate
  2. extractionThe aqueous portion was extracted with dichloromethane (1×1 ml)
  3. customThe combined organic solutions were evaporated
  4. customleaving a yellow oil that solidified on overnight storage in a freezer
  5. customThe residue was purified by flash chromatography on a 170×25 mm silica gel 60 column
  6. washeluted with acetonitrile (150 ml), 5% methanol in acetonitrile (500 ml), and 10% methanol in acetonitrile (250 ml)
  7. customcollecting 15×50 ml fractions
  8. additionFractions containing the product
  9. customwere evaporated

Sources & evidence

ORD record
ord-8de88e50432649ca9a772dbf2251cccf
Source dataset
uspto-grants-2011_02
Patent number
US07888526B2

Reaction notes

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