Dichloromethane → HCID 68592948, compound

HRID 1869799Notes

Reaction equation

HRID 1869799 reaction equation
C(OC(NC(=C[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:31])[CH:18]=[CH:17]2)C([O-])=O)=O)(C)(C)C.F[C:33](F)(F)[C:34]([OH:36])=O.[C:39]([O-:42])(O)=[O:40].[Na+].[CH2:44](Cl)Cl>C1(OC)C=CC=CC=1>[Cl:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:31])[C:24]=1[C:19]1[CH:18]=[CH:17][C:16]2[C:21](=[CH:22][CH:23]=[C:14]([CH:33]=[C:34]([OH:36])[C:39]([O:42][CH3:44])=[O:40])[CH:15]=2)[N:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86619054HCID 86619054, compound

Product 1

HCID 68592948HCID 68592948, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

To a solution of 2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-propenoate 22 (0.48 g) in CH2Cl2 (2 ml) are added at 0° C. two drops of anisole and 1.6 ml of trifluoroacetic acid. The solution is stirred for 2 h and a solution of NaHCO3 saturated is added to reach a basic pH. The aqueous phase is extracted with AcOEt (3×10 ml). The organic phases are washed with brine, dried over MgSO4 and concentrated. The residue is washed with methanol to give methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-hydroxy-2-propenoate 23.

Workup

  1. extractionThe aqueous phase is extracted with AcOEt (3×10 ml)
  2. washThe organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. washThe residue is washed with methanol

Sources & evidence

ORD record
ord-cda5cf4da5344e7fbd6784b2af686571
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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