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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 408971Generated: October 25, 2026

Dichloromethane → (2S)-propyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate

https://huagongshe.com/reaction/408971

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
Reactantp-ToluenesulfonateHCID 85570—
Reactant1-DichlorophosphoryloxynaphthaleneHCID 575631—
ReactantPropyl (2S)-2-aminopropanoateHCID 13742990—
Product(2S)-propyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoateHCID 8666256382%

Reaction Steps

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-propyl 2-aminopropanoate (2.00 g, 11.93 mmol), naphth-1-yl phosphorodichloridate (3.11 g, 11.93 mmol) and TEA (3.32 mL, 23.86 mmol) in 30 mL of dry DCM, were combined to give (2S)-propyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate in 82% yield (3.50 g), as a clear, yellow, thick oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08759318B2
Source datasetuspto-grants-2014_06
ORD IDord-0d2b0f3b14104d6b988b39e944bffe61
Source noteuspto-grants-2014_06