Hydrochloric Acid → Diethyl(2-((tert-butoxycarbonyl)amino)ethyl)(cyclopropyl)malonate

HRID 714920

Reaction equation

[CH:1]1([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].O1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])S1(=O)=O.Cl>CN(C)C=O>[CH2:13]([O:12][C:10](=[O:11])[C:4]([CH2:21][CH2:20][NH:19][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH:1]1[CH2:3][CH2:2]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of diethyl cyclopropylmalonate (7.7 g) obtained in Step A of Example 388 in N,N-dimethylformamide (90 mL) was added sodium hydride (60% in mineral oil, 1.8 g), and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added tert-butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (9.4 g) at the same temperature, and the mixture was stirred at 0° C. for 2 hr. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and 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 (6.7 g).

Workup

stirringthe mixture was stirred at 0° C. for 2 hr
extractionthe mixture was extracted with ethyl acetate
washThe obtained organic layer was washed with water and 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-5794d271586e43f4bd5ee8e6613b8f76
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Linked notes

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