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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1050995Generated: October 31, 2026

Water → Methyl 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]cyclobutylidene]acetate

https://huagongshe.com/reaction/1050995

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantAcetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 17453—
Reactanttert-Butyl 3-oxocyclobutylcarbamateHCID 23374584—
SolventTolueneHCID 1140—
ProductMethyl 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]cyclobutylidene]acetateHCID 233745831,450.6%

Reaction Steps

To a solution of (3-oxo-cyclobutyl)-carbamic acid tert-butyl ester (5.6 g, 30 2 mmol) in anhydrous toluene (100 mL) was added methyl (triphenylphosphoranylidene)acetate (10.7 g, 45.4 mmol) and heated to reflux overnight under N2. After cooling to room temperature, the mixture was poured into water and extracted with EA. The organic phase was dried over Na2SO4, concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (eluted with PE:EA=20:1) to give the title compound (7 g, yield 96%) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09388148B2
Source datasetuspto-grants-2016_07
ORD IDord-12270812d1804ee3aadb417f20cc2b9a
Source noteuspto-grants-2016_07