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

HRID 536638

Reaction equation

HRID 536638 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]1

Participants

4

Reactant 2

HCID 9954069N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonateHCID 86656208HCID 86656208, compound

Product 1

HCID 669417754-Methoxy-9-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-trien-10-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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) is 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

  1. customThen, the pyridine is removed under reduced pressure
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted twice with dichloromethane
  4. washThe combined organic phases are washed with 1 M hydrochloric acid, 1 M NaOH solution, and water
  5. dry with materialAfter drying (MgSO4)
  6. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-be2ab3346de140baa63765b2ac1f6b83
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Linked notes

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