2-Dimethylaminopyridine → HCID 15780123, compound

HRID 1463970Notes

Reaction equation

HRID 1463970 reaction equation
[NH2:1][CH:2]([P:6](=[O:11])([O:9][CH3:10])[O:7][CH3:8])[CH:3]([CH3:5])[CH3:4].C(N(C(C)C)CC)(C)C.CN(C1C=CC=CN=1)C.[C:30]([CH2:34][CH2:35][C:36](Cl)=[O:37])([O:32][CH3:33])=[O:31]>N1C=CC=CC=1>[C:30]([CH2:34][CH2:35][C:36]([NH:1][CH:2]([P:6](=[O:11])([O:7][CH3:8])[O:9][CH3:10])[CH:3]([CH3:5])[CH3:4])=[O:37])([O:32][CH3:33])=[O:31]

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 81531DiisopropylethylamineHCID 12504644HCID 12504644, compound

Product 1

HCID 15780123HCID 15780123, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of a compound of formula 3, preferably dimethyl (1-amino-2-methylpropyl)phosphonate, in an anhydrous polar aprotic solvent, preferably pyridine, is added a tertiary amine, preferably a mixture of tertiary amines, and most preferably, a mixture of diisopropylethylamine and dimethylaminopyridine. The mixture is cooled, preferably to 0° C, and a carboalkoxyalkyl halide, preferably carbomethoxypropionyl chloride is added. The reaction is allowed to stir until the reaction is complete. The product, a compound of Formula 4, preferably dimethyl [1-[N-(3-carbomethoxypropionyl)amino]-2-methylpropyl]phosphonate, may be isolated and purified by conventional means.

Sources & evidence

ORD record
ord-3580a5157db045b3a7b59aa2a9d84d16
Source dataset
uspto-grants-1994_04
Patent number
US05302707

Reaction notes

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