Benzyl Alcohol → 6-Butyl-4-benzyloxycarbonyl-2-oxo-1,2-dihydropyridine

HRID 1708145Notes

Reaction equation

HRID 1708145 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C2N=NNC=2C=CC=1.[CH2:19]([C:23]1[NH:24][C:25](=[O:32])[CH:26]=[C:27]([CH:31]=1)[C:28](O)=[O:29])[CH2:20][CH2:21][CH3:22].C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C>CN(C=O)C>[CH2:19]([C:23]1[NH:24][C:25](=[O:32])[CH:26]=[C:27]([C:28]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:29])[CH:31]=1)[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 540903426-Butyl-2-oxo-1,2-dihydro-isonicotinic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 233520986-Butyl-4-benzyloxycarbonyl-2-oxo-1,2-dihydropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

13.3 g (123 mmol) of benzyl alcohol and 4.7 g (31 mmol) of hydroxybenzotriazole are added to a solution of 6.0 g (31 mmol) of 6-butyl-2-oxo-1,2-dihydro-isonicotinic acid in 100 ml of DMF. The resulting clear solution is cooled to 0° C. followed by the addition of 7.0 g (34 mmol) of dicyclohexylcarbodiimide and 4.2 ml (31 mmol) of triethylamine. The mixture is allowed to thaw at 20° C., stirred for a further 2 hours and subjected to aqueous work-up. 6.8 g (77%) of theory of the title compound are obtained.

Workup

  1. customthaw at 20° C.

Sources & evidence

ORD record
ord-94d8824672464c03990f76084d5817a4
Source dataset
uspto-grants-1994_10
Patent number
US05356911

Reaction notes

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