4-Hydroxymethylpyridine → 2-[(Benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid pyridin-4-ylmethyl ester

HRID 750192Notes

Reaction equation

HRID 750192 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:33])[N:12]1[C:21]([C:22]([OH:24])=[O:23])=[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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:53]1[CH:58]=[CH:57][C:56]([CH2:59]O)=[CH:55][CH:54]=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[N:53]1[CH:58]=[CH:57][C:56]([CH2:59][O:23][C:22]([C:21]2[N:12]([N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH3:33])[C:13](=[O:32])[C:14]3[C:19]([C:20]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:18][C:17]([Cl:31])=[CH:16][CH:15]=3)=[O:24])=[CH:55][CH:54]=1

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 66777355Diethylazodicarboxylate tolueneHCID 691557392-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

Product 1

HCID 691570442-[(Benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid pyridin-4-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (150 mg), triphenylphosphine (120 mg), 4-pyridinemethanol (51 mg) and THF (3.0 ml) was added diethyl azodicarboxylate toluene solution (40%, 210 μl) at 0° C. with stirring and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by medium pressure preparative LC (hexane/ethyl acetate=1/1-1/3) to give 2-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid pyridin-4-ylmethyl ester.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=1/1-1/3)

Sources & evidence

ORD record
ord-5f4671cc41ec4d6f805dcd339865134b
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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