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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1048237Generated: October 30, 2026

Ethyl Acetate → Methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetate

https://huagongshe.com/reaction/1048237

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantThionyl ChlorideHCID 24386—
ReactantSodium BicarbonateHCID 516892—
Reactant[(3r,5r,6s)-5-(3-Chlorophenyl)-6-(4-Chlorophenyl)-1-(Cyclopropylmethyl)-2-Oxopiperidin-3-Yl]acetic AcidHCID 56591370—
SolventMethanolHCID 887—
ProductMethyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetateHCID 56591325—

Reaction Conditions

Temperature25 °C

Reaction Steps

To a suspension of 250 mg (0.578 mmol) of 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetic acid (Example 35) in MeOH (3 mL) was added thionyl chloride (78.0 μl, 1070 μmol) dropwise at 0° C. After being stirred at 25° C. for 14 h, the reaction was diluted (EtOAc), basified (sat NaHCO3), extracted (2×EtOAc). The combined organic layers were washed with sat. aq. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure to provide the title compound as a colorless liquid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08569341B2
Source datasetuspto-grants-2013_10
ORD IDord-4c71c4b8d868408abb34e4e565bb5098
Source noteuspto-grants-2013_10