Oxalyl chloride → 2-[(Benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride

HRID 750187Notes

Reaction equation

HRID 750187 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:33])[N:12]1C(C(O)=O)=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:31])[CH:18]=2)[C:13]1=[O:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34](Cl)(=O)[C:35]([Cl:37])=[O:36]>C1COCC1.CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]([CH3:33])[N:12]1[C:34]([C:35]([Cl:37])=[O:36])=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:31])[CH:18]=2)[C:13]1=[O:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 691557392-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

Product 1

HCID 865995552-[(Benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-[(Benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (300 mg) was dissolved in THF (6.0 ml), and oxalyl chloride (122 μl) and DMF (1 drop) were added at 0° C. with stirring, and the mixture was stirred at room temperature for 2 hrs. and concentrated under reduced pressure. Toluene was added to the residue and they were boiled together several times and dried to give 2-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonyl chloride.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. concentrationand concentrated under reduced pressure
  3. additionToluene was added to the residue and they
  4. customdried

Sources & evidence

ORD record
ord-16688f024a814c95aad4558dc9d3167f
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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