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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2277164Generated: October 31, 2026

Triphenylphosphine → tert-Butyl {(2S)-1-[(4-chloro-5-nitropyridin-2-yl)oxy]propan-2-yl}carbamate

https://huagongshe.com/reaction/2277164

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
Reactant1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 7023103—
ReactantDIAD tolueneHCID 66880968—
ReactantHCID 178526833HCID 178526833—
SolventTetrahydrofuranHCID 8028—
Producttert-Butyl {(2S)-1-[(4-chloro-5-nitropyridin-2-yl)oxy]propan-2-yl}carbamateHCID 8673121745.2%

Reaction Steps

To a solution of 4-chloro-5-nitropyridin-2-ol (1.00 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (1.51 g) and triphenylphosphine (2.25 g) in THF (10 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 4.52 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (860 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09133129B2
Source datasetuspto-grants-2015_09
ORD IDord-e74d8aefbfc34a3b96417dba1ee9428c
Source noteuspto-grants-2015_09