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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1694888Generated: November 2, 2026

Toluene → HCID 178448140, compound

https://huagongshe.com/reaction/1694888

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
ReactantN-{(S)-2-hydroxy-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideHCID 54578740—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178448140HCID 17844814089.7%

Reaction Steps

5.9 ml of a solution of diethyl azodicarboxylate in toluene (40%) (12.9 mmol) was added to a solution of 4.00 g of N-{(S)-2-hydroxy-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide obtained in Example (1f) (10.7 mmol) and 3.38 g of triphenylphosphine (12.9 mmol) in tetrahydrofuran (100 ml) under ice-cooling over 10 minutes, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1) to obtain 3.40 g of the title compound (yield: 89%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158790B2
Source datasetuspto-grants-2012_04
ORD IDord-d0ba49a87dab436ea5f45d0c49541fbc
Source noteuspto-grants-2012_04