N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate → 4-Methoxy-9-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-trien-10-one
Reaction equation
[Cl-].[C:2]([CH2:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH:8]([NH3+:17])[CH2:7]1)(O)=[O:3].COS(C1C=CC(C)=CC=1)(=O)=O.C1(N=C=NCCN2CCOCC2)CCCCC1>N1C=CC=CC=1>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]1[CH2:7][CH:6]2[CH2:5][C:2](=[O:3])[NH:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Carboxymethyl-5-methoxy-indan-1-yl-ammonium chloride (13.2 g) and 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide methyl-p-toluenesulfonate (21.7 g) dissolved in pyridine (500 mL) are stirred at room temperature for 7 d. Then, the pyridine is removed under reduced pressure and the residue is taken up in water (200 mL) and dichloromethane (200 mL). The organic phase is separated and the aqueous phase is extracted twice with dichloromethane. The combined organic phases are washed with 1 M hydrochloric acid, 1 M NaOH solution, and water. After drying (MgSO4), the solvent is evaporated under reduced pressure to yield the product as a beige solid.
Workup
- customThen, the pyridine is removed under reduced pressure
- customThe organic phase is separated
- extractionthe aqueous phase is extracted twice with dichloromethane
- washThe combined organic phases are washed with 1 M hydrochloric acid, 1 M NaOH solution, and water
- dry with materialAfter drying (MgSO4)
- customthe solvent is evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-04ac5996368e4de193090831d89d53fa
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073870B2
Reaction notes
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