Hydrochloric Acid → Diethyl 2-benzyloxycarbonylamino-2-(methoxycarbonylmethyl)malonate

HRID 57742

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34].Cl>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH2:32][C:33]([O:35][CH3:36])=[O:34])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of diethyl 2-benzyloxycarbonylaminomalonate (3.0 g), potassium carbonate (1.6 g), potassium iodide (0.19 g), and methyl 2-bromoacetate (1.9 g) in DMF (50 mL) was stirred at 50° C. for 1 hour. The reaction mixture was cooled, and then poured into diluted hydrochloric acid, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, in which elution was performed with n-hexane/ethyl acetate (4:1) for purification, and then crystallized from ethyl acetate/n-hexane to obtain the title compound (3.52 g, yield: 95%) as colorless oil.

Workup

temperatureThe reaction mixture was cooled
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
washthe residue was subjected to silica gel column chromatography, in which elution
customwas performed with n-hexane/ethyl acetate (4:1) for purification
customcrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-995c581b90244a03a1e384a2adaad932
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434737B2

Linked notes

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