Hydrochloric Acid → Diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate

HRID 57735

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+].Cl[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].Cl>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[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 (5.0 g), potassium carbonate (2.7 g), potassium iodide (0.27 g), and ethyl 2-chloroacetate (2.6 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 crystallized from ethyl acetate/n-hexane to obtain the title compound (5.5 g, yield: 86%) as colorless crystals.

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
customthe residue was crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-3894c10f70494b50b9b7b28ab01b5f7e
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434737B2

Linked notes

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