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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 341869Generated: October 26, 2026

Dimethylformamide → 167356-39-0

https://huagongshe.com/reaction/341869

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium BicarbonateHCID 516892—
ReactantChloromethyl butanoateHCID 2725008—
Reactant(4R)-1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acidHCID 22884797—
Product167356-39-0HCID 2288479970%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a stirred mixture of (4R)-1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid (2.93 g, 8.23 mmol) and sodium bicarbonate (1.38 g, 16.5 mmol) in DMF (150 ml) under nitrogen atmosphere was added chloromethyl butyrate (1.72 g, 12.6 mmol). The reaction mixture was heated at 80° C. for 17 h. Workup by filtration followed by evaporation of solvent. The crude residue was chromatographed on silica gel with 5% ethyl acetate in dichloromethane. Recrystallization from diisopropylether gave colorless crystals (2.62 g, 70%), mp. 128°-129° C. NMR spectral data are identical with the data of the racemate as shown in Example 3. [α]D20 =+17.5° (1% in methanol).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05856346
Source datasetuspto-grants-1999_01
ORD IDord-87aacaf89f584194a518128384d95ddc
Source noteuspto-grants-1999_01