Hydrochloric Acid → HCID 19780809, compound

HRID 2081145Notes

Reaction equation

[Na].[Cl:2][C:3]1[CH:19]=[C:18]([F:20])[C:17]([NH:21][C:22](=[O:33])[CH2:23][C:24]([NH:27][C:28](OCC)=[O:29])=[CH:25][CH3:26])=[CH:16][C:4]=1[C:5]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6].Cl>OC(C)(C)C(OCC)=O>[Cl:2][C:3]1[CH:19]=[C:18]([F:20])[C:17]([N:21]2[C:22](=[O:33])[CH:23]=[C:24]([CH2:25][CH3:26])[NH:27][C:28]2=[O:29])=[CH:16][C:4]=1[C:5]([O:7][C:8]([CH3:14])([CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6]

Participants

Conditions

Temperature: 120 °C

Procedure

0.6 g of sodium is dissolved completely in 50 ml of ethyl α-hydroxyisobutyrate. This solution is combined with the crude ethyl 2-{2-chloro-4-fluoro-5-[3-(ethoxycarbonyl)amino-pent-3-enoyl]amino-benzoyloxy}-2-methylpropionate and stirred at 120° C. for 4 hours. After cooling,this reaction mixture is introduced into 100 ml of 1N hydrochloric acid at 0° C. The mixture is extracted twice with 150 ml of ethyl acetate each time, back-washed twice with 200 ml of water each time, dried over anhydrous magnesium sulphate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel with ethyl acetate/n-hexane (3:2). There is obtained ethyl 2-{2-chloro-4-fluoro-5-[3,6-dihydro-2,6-dioxo-4-ethyl-1(2H)-pyrimidinyl]-benzoyloxy}-2-methylpropionate which is recrystallized from diethyl ether/n-hexane; m.p. 166°-167° C.

Workup

extractionThe mixture is extracted twice with 150 ml of ethyl acetate each time
washback-washed twice with 200 ml of water each time
dry with materialdried over anhydrous magnesium sulphate
concentrationconcentrated under reduced pressure
customThe residue is purified by chromatography on silica gel with ethyl acetate/n-hexane (3:2)

Sources & evidence

ORD record: ord-5f830d83d3a5407d896d26797db468d1
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05183492

Reaction notes

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