Water → HCID 178468323, compound

HRID 1747770Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][N:15]=[C:16]([C:20](=[O:22])[CH3:21])[C:17](=[O:19])[CH3:18])([CH3:6])([CH3:5])[CH3:4].[CH2:23]([O:30][CH2:31][C:32](Cl)=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1COCC1>[CH2:23]([O:30][CH2:31][C:32](=[O:33])[CH2:21][C:20](=[O:22])[C:16](=[N:15][NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][C:3]([CH3:6])([CH3:4])[CH3:5])[C:17](=[O:19])[CH3:18])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (4.28 g) was suspended in THF (30 mL), and a solution of 3-[(2-tert-butoxyphenyl)hydrazono]pentane-2,4-dione (7.47 g) in THF (100 mL) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 40 min, a solution of (benzyloxy)acetylchloride (5.55 mL) in THF (20 mL) was added at 0° C., and the mixture was stirred at 0° C. for 5 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (5.58 g).

Workup

stirringthe mixture was stirred at 0° C. for 5 hr
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-70277f035a7f45099e362c13a661645d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150588B2

Reaction notes

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