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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 63687Generated: October 29, 2026

4-Toluenesulfonyl chloride → (2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester

https://huagongshe.com/reaction/63687

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Toluenesulfonyl chlorideHCID 7397—
ReactantTriethylamineHCID 8471—
Reactant(2R,3S)-Methyl 2-amino-3-hydroxy-4-methylpentanoateHCID 89995944—
SolventDichloromethaneHCID 6344—
Product(2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl esterHCID 90000943—

Reaction Steps

A mixture of (2S,3R)-2-amino-3-hydroxy-4-methyl-pentanoic acid methyl ester (0.50 g, 3.4 mmol) and triethylamine (0.69 g, 6.8 mmol) in dichloromethane (10 mL) was added 4-methyl-benzenesulfonyl chloride (0.71 g, 3.7 mmol) at 0° C. After stirring for 2 hours at room temperature, the mixture was washed with water and the organic layer was separated and then dried over sodium sulfate. After removal of solvent, the residue was used in next step without purification. MS: calc'd (MH+) 316, measured (MH+) 316.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09447086B2
Source datasetuspto-grants-2016_09
ORD IDord-14ebf1bd860147438186f01ac5e90a16
Source noteuspto-grants-2016_09