Triethylamine → 2-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

HRID 750186Notes

Reaction equation

HRID 750186 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([NH:13][CH3:14])[C:6]([C:15]([OH:17])=[O:16])=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:35]([O:34][C:32]([N:13]([CH3:14])[N:7]1[C:6]([C:15]([OH:17])=[O:16])=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[C:8]1=[O:12])=[O:33])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 230605106-chloro-2-methylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

Product 1

HCID 691557392-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (76 ml) of 6-chloro-2-methylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (3.8 g) in THF were added triethylamine (4.0 ml) and benzyl chloroformate (3.6 ml) at 0° C. with stirring, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-dichloromethane/methanol/acetic acid=50/10/1) to give the title compound (2.5 g) as yellow powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-dichloromethane/methanol/acetic acid=50/10/1)

Sources & evidence

ORD record
ord-4fc5a82104c74cb29e005ad4406a088e
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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