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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1443439Generated: October 29, 2026

Acetic Acid → 17-Hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid ethyl ester

https://huagongshe.com/reaction/1443439

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantLithium HydroxideHCID 3939—
Reactant13-Methyl-17-(4-nitro-benzoyloxy)-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.0*4,6*]-octadec-7-ene-4-carboxylic acid ethyl esterHCID 68413090—
SolventMethanol tetrahydrofuran waterHCID 21892291—
Product17-Hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid ethyl esterHCID 68410372—

Reaction Conditions

Temperature0 °C

Reaction Steps

Compound 50 (200 mg, 0.38 mmol) was dissolved in a mixture of methanol/THF/water, 1:2:1, (20 ml) and cooled on ice-bath. Lithium hydroxide (1.9 ml, 1M) was added slowly. The mixture was stirred for 4 h at 0° C., then neutralized with aqueous acetic acid (20 ml) and extracted with dichloromethane. The organic phase was washed with bicarbonate, water, brine and dried over magnesium sulfate. Purification by chromatography (2% methanol in dichloromethane→4%) gave the title compound as a greyish powder (80%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07659245B2
Source datasetuspto-grants-2010_02
ORD IDord-dce5e5675fe14b4b80c71d4fc0ee770d
Source noteuspto-grants-2010_02