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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1445427Generated: October 25, 2026

Methanol → 18-Hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester

https://huagongshe.com/reaction/1445427

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantWaterHCID 962—
ReactantLithium HydroxideHCID 3939—
Reactant14-(4-Methoxy-benzyl)-18-(4-nitro-benzoyloxy)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl esterHCID 66870501—
SolventAcetic AcidHCID 176—
SolventTetrahydrofuranHCID 8028—
Product18-Hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl esterHCID 6687090967%

Reaction Conditions

Temperature0 °C

Reaction Steps

Crude compound 133 (445 mg) was dissolved in THF (20 ml), MeOH (10 ml) and water (10 ml). After cooling to 0° C. 1M LiOH (2 ml) was added. After 1.5 h the hydrolysis was completed and HOAc (1 ml) was added and the solution was evaporated to appr 10 ml. Water was added and the mixture was extracted with DCM (2×30 ml). The pooled organic phase was washed with NaHCO3 (aq), water, brine and dried over MgSO4. The crude product was purified by column chromatography on silica (DCM/MeOH: 100/0-80/20) to give the title compound (201 mg, 67%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07666834B2
Source datasetuspto-grants-2010_02
ORD IDord-fb840f8f861d43cfa27c216f6477f094
Source noteuspto-grants-2010_02