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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 63688Generated: October 30, 2026

Triethylamine → (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester

https://huagongshe.com/reaction/63688

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant(2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl esterHCID 90000943—
ReactantHCID 91658733HCID 91658733—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
Product(2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl esterHCID 89995945—

Reaction Steps

A mixture of (2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester (0.4 g, 1.27 mmol) and diphenylvinylsulfonium triflate (0.5 g, 1.4 mmol) in dichloromethane (10 mL) was added triethylamine dropwise at 0° C. After stirring for 12 hours, the mixture was diluted with water, and then extracted with ethyl acetate, then dried over sodium sulfate. After removal of solvent, the residue was purified by flash chromatopraphy (eluented with ethyl acetate/hexane=1:4) to afford the product as a white solid. MS: calc'd (MH+) 342, measured (MH+) 342.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09447086B2
Source datasetuspto-grants-2016_09
ORD IDord-9c044b0d60d347c288a633b47d8a2491
Source noteuspto-grants-2016_09