Water → (+/-)-ethyl N-[(4-chlorophenyl)(2,3-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)-methyl]-N-[(cyanoimino)methyl]glycine

HRID 1739819Notes

Reaction equation

HRID 1739819 reaction equation
Br[CH2:2][C:3]([O:5]CC)=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:34][CH:35]=[N:36][C:37]#[N:38])[C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[C:21](=[O:27])[CH:20]=[C:19]3[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:11][CH:10]=1.[K].[CH3:40][C:41](O)(C)C.O>CS(C)=O.C(OCC)(=O)C>[CH2:40]([CH:2]([C:3]([OH:5])=[O:4])[N:34]([CH:15]([C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=1)[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH3:26])[C:21](=[O:27])[CH2:20][CH:19]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:35]=[N:36][C:37]#[N:38])[CH3:41]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 86639980Potassium tert-butoxideHCID 178481484HCID 178481484, compound

Product 1

HCID 131721408(+/-)-ethyl N-[(4-chlorophenyl)(2,3-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)-methyl]-N-[(cyanoimino)methyl]glycine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-bromoacetate (2.45 ml) was added dropwise at 5° C. to a solution of intermediate (5-c) (9 g) and 2-methyl-2-propanol potassium salt (2.37 g) in dimethyl sulfoxide (100 ml) and the mixture was stirred at room temperature overnight. Water and ethyl acetate were added, the organic layer was decanted, dried (MgSO4), filtered off and evaporated till dryness. The product was used without further purification, yielding (±)-ethyl N-[(4-chlorophenyl)(2,3-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)-methyl]-N-[(cyanoimino)methyl]glycine (interm. 5-d).

Workup

  1. customthe organic layer was decanted
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered off
  4. customevaporated till dryness
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-5be834ba07444178ac98f75f59936605
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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