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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1186629Generated: October 31, 2026

Sodium Bicarbonate → 4-fluoro-2-((S)-2-methoxy-1-methyl-ethylamino)-benzoic acid tert-butyl ester

https://huagongshe.com/reaction/1186629

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
Reactant2-Propanamine, 1-methoxy-, (2S)-HCID 7021536—
ReactantTert-butyl 2,4-difluorobenzoateHCID 57447335—
Product4-fluoro-2-((S)-2-methoxy-1-methyl-ethylamino)-benzoic acid tert-butyl esterHCID 6673735984%

Reaction Conditions

Temperature65 °C

Reaction Steps

A mixture of 2,4-difluoro-benzoic acid tert-butyl ester (30 g, 140.05 mmol) and (S)-2-methoxy-1-methyl-ethylamine (100 mL) was stirred at 65° C. for 2 days. A saturated solution of NaHCO3 was added and the mixture was extracted with dichloromethane (3 times). The organic phase was washed twice with water then with brine, dried over sodium sulfate filtered and evaporated to dryness to obtain a crude, which was purified by column chromatography on silica gel (exane/ethyl acetate 9:1). The title compound (33.38 g, 84%) was obtained as oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08673893B2
Source datasetuspto-grants-2014_03
ORD IDord-0cd44c771fe6472ab4b19eac3f8db75e
Source noteuspto-grants-2014_03